NP-MRD: Showing NP-Card for Urushiol (15:2) (NP0139008)

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Record Information

Version

2.0

Created at

2022-06-29 19:35:31 UTC

Updated at

2022-06-29 19:35:31 UTC

NP-MRD ID

NP0139008

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Urushiol (15:2)

Description

(8Z,11Z)-urushiol III, also known as urushiol (C15:2) Or urushiol III, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. It was first documented in 2002 (PMID: 12530478). Based on a literature review very few articles have been published on (8Z,11Z)-urushiol III (PMID: 27548435).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 55  0  0  0  0  0  0  0  0999 V2000
    8.5266    0.5142    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5889   -0.5539    0.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5540   -0.9279   -0.4784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7309    0.2300   -0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454    0.2623   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6717   -0.8478   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096   -0.2788    1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7209   -0.2395    1.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7391   -0.7458    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1919    0.4015   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9420    1.0057    0.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8860    2.0628    0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1756    1.8770   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838    1.0448   -1.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242   -0.4231   -0.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6346   -0.6986   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5161   -0.9870    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6674   -1.2306    1.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9033   -1.1894    1.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0328   -0.8978    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3221   -0.8752   -0.4500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046   -0.6578   -0.6820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0013   -0.3674   -2.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8976    1.4334   -0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0022    0.2634   -0.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2287    0.7549    0.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1415   -0.2032    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1956   -1.4655    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575   -1.8713   -0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2010   -1.1446   -1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2567    1.1160   -1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8390    1.1415   -1.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3142   -1.7207    0.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9410   -1.2431   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.1525    1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068    0.2135    2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1843   -1.1128   -0.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -1.5288    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819    1.1818   -0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6908    0.1041   -1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452    1.3980    1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103    0.1739    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893    2.8379   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0984    2.7273    1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6403    2.9199   -0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667    1.5548    0.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5705    1.2276   -1.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401    1.3630   -1.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5533   -0.9977   -1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986   -0.8711   -0.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5327   -1.0261    1.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5545   -1.4553    3.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7778   -1.3867    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5837   -0.6841   -1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9012   -0.3304   -2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 22  2  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 23 55  1  0
 21 54  1  0
 19 53  1  0
 18 52  1  0
 17 51  1  0
M  END


  Mrv1652306292221352D          

 23 23  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 18 22  1  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139008

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C/C\C=C/CCCCCCCC1=C(O)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(22)21(19)23/h4-5,7-8,15,17-18,22-23H,2-3,6,9-14,16H2,1H3/b5-4-,8-7-

> <INCHI_KEY>
RMTXUPIIESNLPW-UTOQUPLUSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.485

> <EXACT_MASS>
316.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.15933143832427

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzene-1,2-diol

> <ALOGPS_LOGP>
7.70

> <JCHEM_LOGP>
7.379654558666667

> <ALOGPS_LOGS>
-5.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.983379271678096

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.548682588012248

> <JCHEM_PKA_STRONGEST_BASIC>
-6.279935694327706

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
101.70819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.60e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(8Z,11Z)-pentadeca-8,11-dien-1-yl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.672  -9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   18                                                            
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
Urushiol (C15:2)	ChEBI
Urushiol III	ChEBI

Chemical Formula

C₂₁H₃₂O₂

Average Mass

316.4850 Da

Monoisotopic Mass

316.24023 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC\C=C/C\C=C/CCCCCCCC1=C(O)C(O)=CC=C1

InChI Identifier

InChI=1S/C21H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(22)21(19)23/h4-5,7-8,15,17-18,22-23H,2-3,6,9-14,16H2,1H3/b5-4-,8-7-

InChI Key

RMTXUPIIESNLPW-UTOQUPLUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

32697561

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12444628

PDB ID

6F8

ChEBI ID

140612

Good Scents ID

Not Available

References

General References

Nagabhushana KS, Umamaheshwari S, Tocoli FE, Prabhu SK, Green IR, Ramadoss CS: Inhibition of soybean and potato lipoxygenases by bhilawanols from bhilawan (Semecarpus anacardium) nut shell liquid and some synthetic salicylic acid analogues. J Enzyme Inhib Med Chem. 2002 Aug;17(4):255-9. doi: 10.1080/1475636021000006243. [PubMed:12530478 ]
Kim JH, Hu Y, Yongqing T, Kim J, Hughes VA, Le Nours J, Marquez EA, Purcell AW, Wan Q, Sugita M, Rossjohn J, Winau F: CD1a on Langerhans cells controls inflammatory skin disease. Nat Immunol. 2016 Oct;17(10):1159-66. doi: 10.1038/ni.3523. Epub 2016 Aug 22. [PubMed:27548435 ]

Showing NP-Card for Urushiol (15:2) (NP0139008)

MOL for NP0139008 (Urushiol (15:2))

3D MOL for NP0139008 (Urushiol (15:2))

3D SDF for NP0139008 (Urushiol (15:2))

3D-SDF for NP0139008 (Urushiol (15:2))

PDB for NP0139008 (Urushiol (15:2))

3D PDB for NP0139008 (Urushiol (15:2))

SMILES for NP0139008 (Urushiol (15:2))

INCHI for NP0139008 (Urushiol (15:2))

Structure for NP0139008 (Urushiol (15:2))

3D Structure for NP0139008 (Urushiol (15:2))