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Showing NP-Card for 4-Hydroxyphenylacetonitrile (NP0002742)

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Record Information
Version1.0
Created at2020-11-23 19:39:18 UTC
Updated at2021-08-19 23:59:18 UTC
NP-MRD IDNP0002742
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxyphenylacetonitrile
Provided ByBMRBBMRB logo
Description4-Hydroxybenzeneacetonitrile, also known as 4-hydroxybenzyl cyanide or 4-hydroxyphenylacetate nitrile, belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group. 4-Hydroxybenzeneacetonitrile 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-Hydroxyphenylacetonitrile is found in Chlamydomonas reinhardtii, Drypetes gossweileri and Moringa oleifera. It was first documented in 1998 (PMID: 9677329). Based on a literature review very few articles have been published on 4-Hydroxybenzeneacetonitrile (PMID: 17984079) (PMID: 12711800) (PMID: 15621622).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002742 (4-Hydroxyphenylacetonitrile)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -5.2394   -0.3422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7442   -0.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2489   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537    0.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1096    1.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    1.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2368    0.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320    0.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927   -1.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0974   -1.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294   -1.5983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3685    1.3921    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607    2.6062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297    2.8453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5831   -0.8602    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4438   -2.3344    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467   -2.5734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  1
  3 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
Download

3D MOL for NP0002742 (4-Hydroxyphenylacetonitrile)

NP0002742
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    3.6853   -0.2567   -1.2989 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9819    0.0949   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0765    0.5321    0.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    0.1988    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377   -1.0224    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1658   -1.3498    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9398   -0.4332   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2340   -0.7480   -0.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3869    0.7811   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951    1.1331   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644    1.6346    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463   -0.0056    1.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540   -1.7448    1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5678   -2.3273    0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7959   -0.0766   -1.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834    1.5210   -1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    2.0687   -0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
Download

3D SDF for NP0002742 (4-Hydroxyphenylacetonitrile)


     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -5.2394   -0.3422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7442   -0.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2489   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7537    0.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1096    1.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856    1.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2368    0.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320    0.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927   -1.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0974   -1.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294   -1.5983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3685    1.3921    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9607    2.6062    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297    2.8453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5831   -0.8602    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4438   -2.3344    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467   -2.5734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  1
  3 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
> <DATABASE_ID>
NP0002742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(CC#N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5H2

> <INCHI_KEY>
AYKYOOPFBCOXSL-UHFFFAOYSA-N

> <FORMULA>
C8H7NO

> <MOLECULAR_WEIGHT>
133.1473

> <EXACT_MASS>
133.052763851

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.708892234222006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)acetonitrile

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.3653776503333332

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.094164080096675

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.490824479878434

> <JCHEM_PKA_STRONGEST_BASIC>
-5.958759212245586

> <JCHEM_POLAR_SURFACE_AREA>
44.019999999999996

> <JCHEM_REFRACTIVITY>
38.3258

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
PHBC

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002742 (4-Hydroxyphenylacetonitrile)

NP0002742
     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    3.6853   -0.2567   -1.2989 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9819    0.0949   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0765    0.5321    0.6402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    0.1988    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1377   -1.0224    0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1658   -1.3498    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9398   -0.4332   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2340   -0.7480   -0.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3869    0.7811   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951    1.1331   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644    1.6346    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463   -0.0056    1.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7540   -1.7448    1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5678   -2.3273    0.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7959   -0.0766   -1.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834    1.5210   -1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    2.0687   -0.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10  4  1  0
  3 11  1  0
  3 12  1  0
  5 13  1  0
  6 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
Download

PDB for NP0002742 (4-Hydroxyphenylacetonitrile)

HEADER    PROTEIN                                 15-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-20         0                                  
HETATM    1  C   UNK     0       1.751  -3.505   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.085  -4.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.417  -4.275   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.751  -1.965   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.085  -5.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.417  -5.815   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.085  -1.195   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.751  -6.585   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.418  -0.425   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       1.751  -8.125   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8                                                       
CONECT    6    3    8                                                       
CONECT    7    4    9                                                       
CONECT    8    5   10    6                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0002742 (4-Hydroxyphenylacetonitrile)

COMPND    NP0002742
HETATM    1  N1  UNL     1       3.685  -0.257  -1.299  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.982   0.095  -0.434  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.077   0.532   0.640  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.665   0.199   0.277  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.138  -1.022   0.644  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.166  -1.350   0.318  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.940  -0.433  -0.385  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.234  -0.748  -0.714  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.387   0.781  -0.740  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.095   1.133  -0.429  1.00  0.00           C  
HETATM   11  H1  UNL     1       2.164   1.635   0.738  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.346  -0.006   1.561  1.00  0.00           H  
HETATM   13  H3  UNL     1       0.754  -1.745   1.201  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.568  -2.327   0.619  1.00  0.00           H  
HETATM   15  H5  UNL     1      -3.796  -0.077  -1.228  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.983   1.521  -1.298  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.357   2.069  -0.693  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4   11   12
CONECT    4    5    5   10
CONECT    5    6   13
CONECT    6    7    7   14
CONECT    7    8    9
CONECT    8   15
CONECT    9   10   10   16
CONECT   10   17
END
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SMILES for NP0002742 (4-Hydroxyphenylacetonitrile)

OC1=CC=C(CC#N)C=C1
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INCHI for NP0002742 (4-Hydroxyphenylacetonitrile)

InChI=1S/C8H7NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5H2
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View in JSmol
Synonyms
ValueSource
4-Hydroxybenzyl cyanideChEBI
4-HydroxybenzylcyanideChEBI
4-Hydroxyphenylacetic acid nitrileChEBI
4-HydroxyphenylacetonitrileChEBI
4-Hydroxyphenylacetate nitrileGenerator
(4-Hydroxyphenyl)acetonitrileHMDB
4-(Cyanomethyl)phenolHMDB
p-Hydroxybenzyl cyanideHMDB
p-HydroxyphenylacetonitrileHMDB
PHBCHMDB
4-Hydroxybenzylcyanide, 14C-labeledHMDB
Para-hydroxybenzylcyanideHMDB
4-HydroxybenzeneacetonitrileChEBI
Chemical FormulaC8H7NO
Average Mass133.1473 Da
Monoisotopic Mass133.05276 Da
IUPAC Name2-(4-hydroxyphenyl)acetonitrile
Traditional NamePHBC
CAS Registry NumberNot Available
SMILES
OC1=CC=C(CC#N)C=C1
InChI Identifier
InChI=1S/C8H7NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5H2
InChI KeyAYKYOOPFBCOXSL-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 Origin
Species NameSourceReference
Angelica furcijuga KITAGAWAKNApSAcK Database
Brassica albaKNApSAcK Database
Brassica hirtaKNApSAcK Database
Chlamydomonas reinhardtiiLOTUS Database
Drypetes gossweileriLOTUS Database
Moringa oleiferaLOTUS Database
Sinapis albaFooDB
Sorghum bicolorKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl cyanides
Direct ParentBenzyl cyanides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point67.00 to 71.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point329.00 to 330.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility21970 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.591 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP1.93ALOGPS
logP1.37ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)9.49ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.33 m³·mol⁻¹ChemAxon
Polarizability13.71 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029757
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000961
KNApSAcK IDC00029532
Chemspider ID24729
KEGG Compound IDC03766
BioCyc IDCPD-1074
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound26548
PDB IDNot Available
ChEBI ID16667
Good Scents IDrw1203751
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. Cooksey CJ, Garratt PJ, Land EJ, Ramsden CA, Riley PA: Tyrosinase kinetics: failure of the auto-activation mechanism of monohydric phenol oxidation by rapid formation of a quinomethane intermediate. Biochem J. 1998 Aug 1;333 ( Pt 3):685-91. doi: 10.1042/bj3330685. [PubMed:9677329 ]
  3. Calderon AI, Terreaux C, Gupta MP, Hostettmann K, Schenk KJ: Taxiphyllin from Henriettella fascicularis. Acta Crystallogr C. 2003 Mar;59(Pt 3):o174-6. doi: 10.1107/s0108270103001355. Epub 2003 Feb 28. [PubMed:12711800 ]
  4. Su YF, Zhang ZX, Guo CY, Guo DA: A nobel cyanogenic glycoside from Semiaquilegia adoxoides. J Asian Nat Prod Res. 2005 Apr;7(2):171-4. doi: 10.1080/10286020310001625148. [PubMed:15621622 ]