Np mrd loader

Showing NP-Card for Phenol (NP0000170)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-07 21:52:01 UTC
NP-MRD IDNP0000170
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenol
DescriptionPhenol, is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of micro-organisms including some fungi and viruses, but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 Mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin (Wikipedia). In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2].
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000170 (Phenol)


  Mrv1652309272007402D          

  7  7  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    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
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
Download

3D MOL for NP0000170 (Phenol)

HMDB0000228
     RDKit          3D
Phenol
 13 13  0  0  0  0  0  0  0  0999 V2000
   -2.4586   -0.1783   -0.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0807   -0.0698   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488   -1.2361   -0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0249   -1.1126    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    0.1202    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946    1.2663    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    1.1713   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.2096    0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8235   -2.2070   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5957   -2.0490    0.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7326    0.1774    0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3565    2.2644    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    2.0628   -0.1974 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  2  1  0
  1  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
M  END
Download

3D SDF for NP0000170 (Phenol)


  Mrv1652309272007402D          

  7  7  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    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
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000170

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H

> <INCHI_KEY>
ISWSIDIOOBJBQZ-UHFFFAOYSA-N

> <FORMULA>
C6H6O

> <MOLECULAR_WEIGHT>
94.1112

> <EXACT_MASS>
94.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.812560861971921

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
phenol

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.6696804943333332

> <ALOGPS_LOGS>
-0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.016150276173818

> <JCHEM_PKA_STRONGEST_BASIC>
-5.476712177992348

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
28.038899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000170 (Phenol)

HMDB0000228
     RDKit          3D
Phenol
 13 13  0  0  0  0  0  0  0  0999 V2000
   -2.4586   -0.1783   -0.3421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0807   -0.0698   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488   -1.2361   -0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0249   -1.1126    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    0.1202    0.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946    1.2663    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4720    1.1713   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9998   -0.2096    0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8235   -2.2070   -0.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5957   -2.0490    0.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7326    0.1774    0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3565    2.2644    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0756    2.0628   -0.1974 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  2  1  0
  1  8  1  0
  3  9  1  0
  4 10  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
M  END
Download

PDB for NP0000170 (Phenol)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       1.083   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   0.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.417   1.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   2.832   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.750   3.602   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
Download

3D PDB for NP0000170 (Phenol)

COMPND    HMDB0000228
HETATM    1  O1  UNL     1      -2.459  -0.178  -0.342  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.081  -0.070  -0.190  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.349  -1.236  -0.104  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.025  -1.113   0.048  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.655   0.120   0.113  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.895   1.266   0.024  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.472   1.171  -0.127  1.00  0.00           C  
HETATM    8  H1  UNL     1      -3.000  -0.210   0.512  1.00  0.00           H  
HETATM    9  H2  UNL     1      -0.823  -2.207  -0.153  1.00  0.00           H  
HETATM   10  H3  UNL     1       1.596  -2.049   0.114  1.00  0.00           H  
HETATM   11  H4  UNL     1       2.733   0.177   0.232  1.00  0.00           H  
HETATM   12  H5  UNL     1       1.356   2.264   0.071  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.076   2.063  -0.197  1.00  0.00           H  
CONECT    1    2    8
CONECT    2    3    3    7
CONECT    3    4    9
CONECT    4    5    5   10
CONECT    5    6   11
CONECT    6    7    7   12
CONECT    7   13
END
Download

SMILES for NP0000170 (Phenol)

OC1=CC=CC=C1
Download

INCHI for NP0000170 (Phenol)

InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
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View in JSmol
Synonyms
ValueSource
Acide carboliqueChEBI
Acide pheniqueChEBI
BenzenolChEBI
Carbolic acidChEBI
CarbolsaeureChEBI
HydroxybenzeneChEBI
KarbolsaeureChEBI
OxybenzeneChEBI
Phenic acidChEBI
Phenylic acidChEBI
Phenylic alcoholChEBI
PHOHChEBI
Liquefied phenolKegg
Phenol for disinfectionKegg
Phenol, liquefiedKegg
PaoscleKegg
CarbolateGenerator
PhenateGenerator
PhenylateGenerator
AnbesolHMDB
BenzophenolHMDB
Campho-phenique cold sore gelHMDB
Campho-phenique gelHMDB
Campho-phenique liquidHMDB
Carbolic acid liquidHMDB
Carbolic oilHMDB
Carbolicum acidumHMDB
CarbolsaureHMDB
Cepastat lozengesHMDB
Cuticura pain relieving ointmentHMDB
FenolHMDB
FenoloHMDB
FenosmolinHMDB
FenosmolineHMDB
Hydroxy-benzeneHMDB
IPHHMDB
IZALHMDB
Liquid phenolHMDB
Liquified phenolHMDB
Monohydroxy benzeneHMDB
MonohydroxybenzeneHMDB
MonophenolHMDB
PhenicHMDB
Phenic alcoholHMDB
Phenol alcoholHMDB
Phenol homopolymerHMDB
Phenol liquidHMDB
Phenol moltenHMDB
Phenol polymer-boundHMDB
Phenol solutionHMDB
Phenol syntheticHMDB
Phenolated waterHMDB
Phenolated water for disinfectionHMDB
PhenoleHMDB
PhenosmolinHMDB
Synthetic phenolHMDB
Tea polyphenolHMDB
Phenol, sodium saltHMDB
Phenolate sodiumHMDB
CarbolHMDB
Phenolate, sodiumHMDB
Sodium phenolateHMDB
Chemical FormulaC6H6O
Average Mass94.1112 Da
Monoisotopic Mass94.04186 Da
IUPAC Namephenol
Traditional Namephenol
CAS Registry Number108-95-2
SMILES
OC1=CC=CC=C1
InChI Identifier
InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
InChI KeyISWSIDIOOBJBQZ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, simulated)zinat@ualberta.caNot AvailableNot Available2022-02-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Acacia catechuPlant
Agaricus moelleriLOTUS Database
Agaricus xanthodermusLOTUS Database
Angelica sinensisPlant
Apis ceranaLOTUS Database
Apium graveolens var. dulceFooDB
    • Jian Tang, Yuangang Zhang, Thomas G. Hartman, Robert T. Rosen, and Chi Tang Ho. Free and glycosid...
Artemisia capillarisPlant
Artemisia dracunculusFooDB
Aspalathus linearisLOTUS Database
Asparagus officinalisFooDB
Azadirachta indicaLOTUS Database
Bupleurum chinensePlant
Cannabis sativaCannabisDB
      Not Available
Capsicum annuumFooDB
Carthamus tinctoriusFooDB
Cedronella canariensisLOTUS Database
Cichorium endiviaLOTUS Database
Cinnamomum verumFooDB
Coffea arabicaLOTUS Database
Coffea arabica L.FooDB
Coffea canephoraFooDB
Cyperus conglomeratusLOTUS Database
Daphne papyraceaLOTUS Database
Dipsacus asperoidesPlant
Elsholtzia nipponicaPlant
Evernia prunastriLOTUS Database
Festuca rubraLOTUS Database
Glycine maxFooDB
Glycyrrhiza glabraLOTUS Database
Gossypium hirsutumPlant
Gossypium mexicanumPlant
Homo sapiens (Urine)Animalia
Melia azedarachPlant
MorusFooDB
Morus spp.Plant
Mus musculusLOTUS Database
Myrtus communisLOTUS Database
Origanum majoranaFooDB
Osmorhiza aristataLOTUS Database
Paederia chinensisPlant
Paeonia lactifloraPlant
Paeonia suffruticosaLOTUS Database
Peristeria elataLOTUS Database
Perovskia angustifoliaPlant
Photinia melanocarpaLOTUS Database
Physarum polycephalumLOTUS Database
Pinus sibiricaPlant
Polygala senegaLOTUS Database
Populus tremuloidesPlant
Posidonia oceanicaPlant
Prunus domesticaLOTUS Database
Pueraria montanaLOTUS Database
Quercus roburLOTUS Database
Satureja montanaFooDB
Scrophularia buergerianaLOTUS Database
Scutellaria baicalensisLOTUS Database
Sergia lucensLOTUS Database
Sesamum indicumFooDB
Solanum lycopersicum var. lycopersicumFooDB
Strobilanthes crispusPlant
Tamarindus indicaFooDB
Terminalia chebulaLOTUS Database
Theobroma cacaoLOTUS Database
Trigonella foenum-graecumLOTUS Database
Ulva lactuca-
Vaccinium corymbosumFooDB
Vaccinium macrocarponLOTUS Database
Vaccinium myrtillusFooDB
Vigna radiataFooDB
Vitex agnus-castusLOTUS Database
Vitex trifoliaPlant
Vitis viniferaLOTUS Database
Zingiber miogaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point40.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility82.8 mg/mL at 25 °CNot Available
LogP1.46Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility46.6 g/LALOGPS
logP1.39ALOGPS
logP1.67ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)10.02ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.04 m³·mol⁻¹ChemAxon
Polarizability9.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000228
DrugBank IDDB03255
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000893
KNApSAcK IDC00002664
Chemspider ID971
KEGG Compound IDC15584
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenol
METLIN IDNot Available
PubChem Compound996
PDB IDNot Available
ChEBI ID15882
Good Scents IDrw1009361
References
General References
  1. Jones AL, Hagen M, Coughtrie MW, Roberts RC, Glatt H: Human platelet phenolsulfotransferases: cDNA cloning, stable expression in V79 cells and identification of a novel allelic variant of the phenol-sulfating form. Biochem Biophys Res Commun. 1995 Mar 17;208(2):855-62. [PubMed:7695643 ]
  2. Kilic SS, Aydin S, Kilic N, Erman F, Aydin S, Celik I: Serum arylesterase and paraoxonase activity in patients with chronic hepatitis. World J Gastroenterol. 2005 Dec 14;11(46):7351-4. [PubMed:16437641 ]
  3. Tanaka T, Kasai K, Kita T, Tanaka N: Distribution of phenol in a fatal poisoning case determined by gas chromatography/mass spectrometry. J Forensic Sci. 1998 Sep;43(5):1086-8. [PubMed:9729832 ]
  4. McDonald TA, Holland NT, Skibola C, Duramad P, Smith MT: Hypothesis: phenol and hydroquinone derived mainly from diet and gastrointestinal flora activity are causal factors in leukemia. Leukemia. 2001 Jan;15(1):10-20. [PubMed:11243376 ]
  5. Blades KJ, Patel S: The dynamics of tear flow within a phenol red impregnated thread. Ophthalmic Physiol Opt. 1996 Sep;16(5):409-15. [PubMed:8944185 ]
  6. Miller WL, Doughty MJ, Narayanan S, Leach NE, Tran A, Gaume AL, Bergmanson JP: A comparison of tear volume (by tear meniscus height and phenol red thread test) and tear fluid osmolality measures in non-lens wearers and in contact lens wearers. Eye Contact Lens. 2004 Jul;30(3):132-7. [PubMed:15499232 ]
  7. Hume R, Barker EV, Coughtrie MW: Differential expression and immunohistochemical localisation of the phenol and hydroxysteroid sulphotransferase enzyme families in the developing lung. Histochem Cell Biol. 1996 Feb;105(2):147-52. [PubMed:8852436 ]
  8. Slatkin NE, Rhiner M: Phenol saddle blocks for intractable pain at end of life: report of four cases and literature review. Am J Hosp Palliat Care. 2003 Jan-Feb;20(1):62-6. [PubMed:12568439 ]
  9. Bauer M, Patzelt D: A method for simultaneous RNA and DNA isolation from dried blood and semen stains. Forensic Sci Int. 2003 Sep 9;136(1-3):76-8. [PubMed:12969623 ]
  10. Norberg J, Emneus JA, Jonsson JA, Mathiasson L, Burestedt E, Knutsson M, Marko-Varga G: On-line supported liquid membrane-liquid chromatography with a phenol oxidase-based biosensor as a selective detection unit for the determination of phenols in blood plasma. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):39-46. [PubMed:9389336 ]
  11. Tucker IG: A method to study the kinetics of oral mucosal drug absorption from solutions. J Pharm Pharmacol. 1988 Oct;40(10):679-83. [PubMed:2907532 ]
  12. Achterrath-Tuckermann U, Saano V, Minker E, Stroman F, Arny I, Joki S, Nuutinen J, Szelenyi I: Influence of azelastine and some selected drugs on mucociliary clearance. Lung. 1992;170(4):201-9. [PubMed:1522740 ]
  13. Tatsumi H, Shimada N, Kuramoto R, Mochizuki Y, Nishizima M, Arai M, Osanai K, Ishihara K, Goso K, Hotta K: [The phenol turbidity test for measurement of pulmonary surfactants in amniotic fluid--rapid test for fetal lung maturity (author's transl)]. Acta Obstet Gynaecol Jpn. 1981 May;33(5):643-50. [PubMed:6894513 ]
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