Np mrd loader

Showing NP-Card for Orcinol (NP0051531)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-27 22:51:45 UTC
Updated at2022-04-27 22:51:46 UTC
NP-MRD IDNP0051531
Secondary Accession NumbersNone
Natural Product Identification
Common NameOrcinol
Description Orcinol is found in Amaranthus hypochondriacus , Asarum kiusianum, Brucea javanica, Calluna vulgaris, Psydrax subcordata, Castanea sativa, Cleyera japonica, Dittrichia viscosa , Erica arborea , Erica umbellata, Lilium leichtlinii, Paraburkholderia phymatum, Parmelia tinctorum, Parmotrema tinctorum, Penicillium citrinum, Punctelia subrudecta, Rhododendron dauricum , Rumex patientia , Verticillium albo-atrum and Vitis vinifera. Orcinol was first documented in 1986 (PMID: 3742332).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051531 (Orcinol)


  Mrv1652302102020362D          

  9  9  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
M  END
Download

3D MOL for NP0051531 (Orcinol)

     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
    2.4398   -0.4738    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760   -0.1929    0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254    1.0530    0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335    1.3072    0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2812    2.5641    0.7625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7582    0.3523    0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -0.8970   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694   -1.9110   -0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606   -1.1566   -0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542    0.1421    0.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -0.1899   -0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6487   -1.5605    0.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2321    1.7910    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3800    3.2684    0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8352    0.5583    0.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039   -2.5161   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3866   -2.1386   -0.6635 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0051531 (Orcinol)


  Mrv1652302102020362D          

  9  9  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  2  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051531

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O2/c1-5-2-6(8)4-7(9)3-5/h2-4,8-9H,1H3

> <INCHI_KEY>
OIPPWFOQEKKFEE-UHFFFAOYSA-N

> <FORMULA>
C7H8O2

> <MOLECULAR_WEIGHT>
124.139

> <EXACT_MASS>
124.052429498

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.860890127795983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methylbenzene-1,3-diol

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.8795365619999997

> <ALOGPS_LOGS>
-0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.840088109341647

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.388006105492794

> <JCHEM_PKA_STRONGEST_BASIC>
-5.6637289951922805

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
35.061

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orcinol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0051531 (Orcinol)

Download
PDB for NP0051531 (Orcinol)
HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    2                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

Download
3D PDB for NP0051531 (Orcinol)
Download
SMILES for NP0051531 (Orcinol)
CC1=CC(O)=CC(O)=C1
Download
INCHI for NP0051531 (Orcinol)
InChI=1S/C7H8O2/c1-5-2-6(8)4-7(9)3-5/h2-4,8-9H,1H3
Download
View in JSmol
Synonyms
ValueSource
1,3-Dihydroxy-5-methylbenzeneChEBI
3,5-DihydroxytolueneChEBI
3,5-ToluenediolChEBI
3-Hydroxy-5-methylphenolChEBI
5-Methyl-1,3-benzenediolChEBI
5-Methyl-1,3-dihydroxybenzeneChEBI
5-MethylresorcinolChEBI
OrcinChEBI
Orcinol, 14C-labeled CPDMeSH
OrzinMeSH
Chemical FormulaC7H8O2
Average Mass124.1390 Da
Monoisotopic Mass124.05243 Da
IUPAC Name5-methylbenzene-1,3-diol
Traditional Nameorcinol
CAS Registry NumberNot Available
SMILES
CC1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C7H8O2/c1-5-2-6(8)4-7(9)3-5/h2-4,8-9H,1H3
InChI KeyOIPPWFOQEKKFEE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Amaranthus hypochondriacusPlant
Asarum kiusianumLOTUS Database
Brucea javanicaLOTUS Database
Calluna vulgarisLOTUS Database
Canthium subcordatumLOTUS Database
Castanea sativaLOTUS Database
Cleyera japonicaLOTUS Database
Dittrichia viscosaPlant
Erica arboreaPlant
Erica umbellataPlant
Lilium leichtliniiLOTUS Database
Paraburkholderia phymatum-
Parmelia tinctorumFungi
Parmotrema tinctorumLOTUS Database
Penicillium citrinumLOTUS Database
Punctelia subrudectaLOTUS Database
Rhododendron dauricumPlant
Rumex patientiaPlant
Verticillium albo-atrumLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassBenzenediols  
Direct ParentResorcinols  
Alternative Parents
Substituents
  • Resorcinol
    • 

  • M-cresol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Toluene
    • 

  • Monocyclic benzene moiety
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP1.01ALOGPS
logP1.88ChemAxon
logS-0.45ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.06 m³·mol⁻¹ChemAxon
Polarizability12.86 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002661  
Chemspider IDNot Available
KEGG Compound IDC00727  
BioCyc IDORCINOL-CPD  
BiGG IDNot Available
Wikipedia LinkOrcinol  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16536  
Good Scents IDNot Available
References
General References
  1. Seshime Y, Juvvadi PR, Kitamoto K, Ebizuka Y, Nonaka T, Fujii I: Aspergillus oryzae type III polyketide synthase CsyA is involved in the biosynthesis of 3,5-dihydroxybenzoic acid. Bioorg Med Chem Lett. 2010 Aug 15;20(16):4785-8. doi: 10.1016/j.bmcl.2010.06.119. Epub 2010 Jun 25. [PubMed:20630753  ] 
  2. Ivanova V, Backor M, Dahse HM, Graefe U: Molecular structural studies of lichen substances with antimicrobial, antiproliferative, and cytotoxic effects from Parmelia subrudecta. Prep Biochem Biotechnol. 2010;40(4):377-88. doi: 10.1080/10826068.2010.525432. [PubMed:21108141  ] 
  3. Tretyakova NY, Lebedev AT, Petrosyan VS: Degradative pathways for aqueous chlorination of orcinol. Environ Sci Technol. 1994 Apr 1;28(4):606-13. doi: 10.1021/es00053a012. [PubMed:22196542  ] 
  4. Kachurin AM, Vasil'ev VB, Soroka NV: [Oxidation of orcinol by ceruloplasmin and mixed-ligand copper complexes]. Biokhimiia. 1989 Jan;54(1):39-45. [PubMed:2719988  ] 
  5. Sahasrabudhe SR, Lala D, Modi VV: Degradation of orcinol by Aspergillus niger. Can J Microbiol. 1986 Jul;32(7):535-8. doi: 10.1139/m86-099. [PubMed:3742332  ]