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Showing NP-Card for 4-Hydroxybenzyl alcohol (NP0002820)

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Record Information
Version2.0
Created at2020-11-23 19:41:15 UTC
Updated at2021-08-19 23:59:26 UTC
NP-MRD IDNP0002820
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxybenzyl alcohol
Provided ByBMRBBMRB logo
Description4-Hydroxybenzyl alcohol, also known as p-methylolphenol or 4-(hydroxymethyl)phenol, belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure. 4-Hydroxybenzyl alcohol exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzyl alcohol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 4-Hydroxybenzyl alcohol is found in Anethum graveolens, Arcangelisia gusanlung, Bacopa monnieri, Bletilla striata, Cucurbita pepo, Galeola faberi, Gymnadenia conopsea, Homo sapiens, Lupinus angustifolius, Dactylorhiza hatagirea, Oxalis pes-caprae, Populus laurifolia and Sorghum halepense. 4-Hydroxybenzyl alcohol was first documented in 2021 (PMID: 34065028). Based on a literature review very few articles have been published on 4-Hydroxybenzyl alcohol.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002820 (4-Hydroxybenzyl alcohol)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    3.7938   -0.1596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938   -0.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938   -0.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415   -1.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -1.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062   -0.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4538    1.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462    1.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5462    1.1381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2965    1.3431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2912   -1.6569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7892   -2.7523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108   -2.7469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538    1.1542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2015    2.4492    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985    2.4438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  1 10  1  0
  2 11  1  6
  2 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

3D MOL for NP0002820 (4-Hydroxybenzyl alcohol)

NP0002820
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -3.0091    0.3647   -0.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2622   -0.4984    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029   -0.2265    0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342   -0.8772   -0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154   -0.6551   -0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    0.2623   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822    0.4733   -0.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1853    0.9382    0.8040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684    0.6887    0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7010    1.2816   -0.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5294   -1.5209   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5501   -0.3004    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5160   -1.5887   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9157   -1.1777   -1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9979   -0.0487    0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6831    1.6592    1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7251    1.2256    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0002820 (4-Hydroxybenzyl alcohol)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    3.7938   -0.1596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938   -0.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938   -0.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415   -1.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -1.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062   -0.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4538    1.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462    1.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5462    1.1381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2965    1.3431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2912   -1.6569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7892   -2.7523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108   -2.7469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538    1.1542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2015    2.4492    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985    2.4438    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  1 10  1  0
  2 11  1  6
  2 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
> <DATABASE_ID>
NP0002820

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H2

> <INCHI_KEY>
BVJSUAQZOZWCKN-UHFFFAOYSA-N

> <FORMULA>
C7H8O2

> <MOLECULAR_WEIGHT>
124.1372

> <EXACT_MASS>
124.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.859823269798696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(hydroxymethyl)phenol

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.9023307269999997

> <ALOGPS_LOGS>
-0.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.211268179700756

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.476300531112695

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7866262189825433

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
34.8548

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.98e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-hydroxybenzyl alcohol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002820 (4-Hydroxybenzyl alcohol)

NP0002820
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -3.0091    0.3647   -0.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2622   -0.4984    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029   -0.2265    0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342   -0.8772   -0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154   -0.6551   -0.9913 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    0.2623   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2822    0.4733   -0.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1853    0.9382    0.8040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1684    0.6887    0.9213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7010    1.2816   -0.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5294   -1.5209   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5501   -0.3004    1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5160   -1.5887   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9157   -1.1777   -1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9979   -0.0487    0.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6831    1.6592    1.4549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7251    1.2256    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9  3  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  4 13  1  0
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

PDB for NP0002820 (4-Hydroxybenzyl alcohol)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    7                                                       
CONECT    5    6                                                            
CONECT    6    1    2    5                                                  
CONECT    7    3    4    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
Download

3D PDB for NP0002820 (4-Hydroxybenzyl alcohol)

COMPND    NP0002820
HETATM    1  O1  UNL     1      -3.009   0.365  -0.607  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.262  -0.498   0.219  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.803  -0.227   0.096  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.034  -0.877  -0.845  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.315  -0.655  -0.991  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.919   0.262  -0.154  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.282   0.473  -0.317  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.185   0.938   0.804  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.168   0.689   0.921  1.00  0.00           C  
HETATM   10  H1  UNL     1      -2.701   1.282  -0.384  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.529  -1.521  -0.099  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.550  -0.300   1.291  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.516  -1.589  -1.490  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.916  -1.178  -1.742  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.998  -0.049   0.168  1.00  0.00           H  
HETATM   16  H7  UNL     1       1.683   1.659   1.455  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.725   1.226   1.675  1.00  0.00           H  
CONECT    1    2   10
CONECT    2    3   11   12
CONECT    3    4    4    9
CONECT    4    5   13
CONECT    5    6    6   14
CONECT    6    7    8
CONECT    7   15
CONECT    8    9    9   16
CONECT    9   17
END
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SMILES for NP0002820 (4-Hydroxybenzyl alcohol)

OCC1=CC=C(O)C=C1
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INCHI for NP0002820 (4-Hydroxybenzyl alcohol)

InChI=1S/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H2
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View in JSmol
Synonyms
ValueSource
p-MethylolphenolChEBI
4-(Hydroxymethyl)phenolHMDB
4-Methylol phenolHMDB
GastrodigeninHMDB
p-Hydroxybenzyl alcoholHMDB
4-(Hydroxymethyl)phenol (acd/name 4.0)HMDB
4-HydroxybenzenemethanolHMDB
4-MethylolphenolHMDB
a-Hydroxy-p-cresolHMDB
alpha-Hydroxy-p-cresolHMDB
b4-Hydroxy-enzenemethanolHMDB
p-(Hydroxymethyl)phenolHMDB
p-Hydroxy-benzyl alcoholHMDB
4-Hydroxybenzyl alcoholChEBI
Chemical FormulaC7H8O2
Average Mass124.1372 Da
Monoisotopic Mass124.05243 Da
IUPAC Name4-(hydroxymethyl)phenol
Traditional NameP-hydroxybenzyl alcohol
CAS Registry NumberNot Available
SMILES
OCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C7H8O2/c8-5-6-1-3-7(9)4-2-6/h1-4,8-9H,5H2
InChI KeyBVJSUAQZOZWCKN-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
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 Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensLOTUS Database
Anser anserFooDB
Arcangelisia gusanlungLOTUS Database
Bacopa monnieriLOTUS Database
Bison bisonFooDB
Bletilla striataLOTUS Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Cucurbita moschataKNApSAcK Database
Cucurbita pepoLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Galeola faberiLOTUS Database
Gallus gallusFooDB
Gastrodia elataKNApSAcK Database
Gymnadenia conopseaLOTUS Database
Gymnadenia conopsea R.BR.KNApSAcK Database
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lupinus angustifoliusLOTUS Database
Malva silvestrisKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
Orchis hatagireaLOTUS Database
OryctolagusFooDB
Ovis ariesFooDB
Oxalis pes-capraeLOTUS Database
Pelargonium reniformeKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Populus laurifoliaLOTUS Database
Sorghum halepenseLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl alcohols
Direct ParentBenzyl alcohols
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point114.00 to 122.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point252.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility6700 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP0.250The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP0.53ALOGPS
logP0.9ChemAxon
logS-0.32ALOGPS
pKa (Strongest Acidic)9.48ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.85 m³·mol⁻¹ChemAxon
Polarizability12.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0011724
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012553
KNApSAcK IDC00029533
Chemspider ID122
KEGG Compound IDC17467
BioCyc ID4-HYDROXY-BENZYL-ALCOHOL
BiGG IDNot Available
Wikipedia LinkGastrodigenin
METLIN IDNot Available
PubChem Compound125
PDB IDNot Available
ChEBI ID67410
Good Scents IDrw1107691
References
General References
  1. Guardiola JJ, Hardesty JE, Beier JI, Prough RA, McClain CJ, Cave MC: Plasma Metabolomics Analysis of Polyvinyl Chloride Workers Identifies Altered Processes and Candidate Biomarkers for Hepatic Hemangiosarcoma and Its Development. Int J Mol Sci. 2021 May 11;22(10). pii: ijms22105093. doi: 10.3390/ijms22105093. [PubMed:34065028 ]