NP-MRD: Showing NP-Card for cardanol monoene (NP0254772)

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Record Information

Version

2.0

Created at

2022-09-07 19:02:32 UTC

Updated at

2022-09-07 19:02:32 UTC

NP-MRD ID

NP0254772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cardanol monoene

Description

(Z)-3-(pentadec-8-en-1-yl)phenol belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. cardanol monoene is found in Anacardium occidentale and Ginkgo biloba. These are phenols that are unsubstituted at the 4-position (z)-3-(pentadec-8-en-1-yl)phenol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 56 56  0  0  0  0  0  0  0  0999 V2000
    7.3584    1.2356   -2.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2101    0.9356   -1.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200    0.2818   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6379   -0.0376    0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6062   -0.9860   -0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412   -1.2729    1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5200   -2.1909    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2588   -1.8479    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648   -0.5685    0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704   -0.8587    1.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228    0.4122    2.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7350    1.1337    1.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8301    0.3190    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8928   -0.0876    1.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9425   -0.8978    0.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5885   -0.1542   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7238    0.5888    0.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3477    1.2967   -0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8623    1.2883   -2.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7266    0.5455   -2.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2414    0.5418   -3.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1041   -0.1612   -1.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9867    1.0469   -3.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6875    2.2860   -2.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1971    0.5130   -2.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7967    1.9359   -1.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4090    0.4056   -2.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267    0.9879    0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3063   -0.6444   -0.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0218   -0.3816    1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0964    0.9327    0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1471   -0.5471   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001   -1.9333   -0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266   -1.7926    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1236   -0.3076    1.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475   -3.2083    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5501   -2.5888    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0980   -0.1750   -0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3226    0.2372    1.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0962   -1.5470    1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854   -1.2913    2.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    1.1291    2.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7431    0.2376    3.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0074    1.4146    0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1634    2.0822    1.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    0.9956   -0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4254   -0.5208    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5027   -0.7353    2.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3075    0.8215    2.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6714   -1.2536    1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4294   -1.8191    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1056    0.5977    1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2412    1.8805   -0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3485    1.8437   -3.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6256   -0.2075   -4.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2094   -0.7409   -1.6798 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  1  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 20  1  0
 20 21  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  0
 15 51  1  0
 22 56  1  0
 21 55  1  0
 19 54  1  0
 18 53  1  0
 17 52  1  0
M  END

(15:1)-Cardanol
  Mrv1572004231619312D          

 22 22  0  0  0  0            999 V2000
   -0.7468    1.8902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3782    1.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2032    1.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6157    2.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1407    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4407    2.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282    0.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9157    2.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3282    1.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0907    2.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1532    1.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8532    3.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9032    0.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6782    3.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5657    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4907    1.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4907   -0.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3907    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3343    1.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3343   -0.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7468    0.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  2  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254772

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-20-17-15-18-21(22)19-20/h7-8,15,17-19,22H,2-6,9-14,16H2,1H3/b8-7-

> <INCHI_KEY>
YLKVIMNNMLKUGJ-FPLPWBNLSA-N

> <FORMULA>
C21H34O

> <MOLECULAR_WEIGHT>
302.502

> <EXACT_MASS>
302.260965715

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.791120437521315

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(8Z)-pentadec-8-en-1-yl]phenol

> <ALOGPS_LOGP>
8.76

> <JCHEM_LOGP>
8.045141537

> <ALOGPS_LOGS>
-6.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.105147601678176

> <JCHEM_PKA_STRONGEST_BASIC>
-5.478421324745946

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
98.61070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.38e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cardanol monoene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: (15:1)-Cardanol                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-16         0                                  
HETATM    1  O   UNK     0      -1.394   3.528   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.306   3.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.846   3.529   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.536   2.195   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.616   4.862   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.996   2.195   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.156   4.862   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.226   0.861   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.776   4.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.546   3.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.236   4.862   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.086   3.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.926   6.196   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.686   0.861   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.466   6.196   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.856   2.195   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.916   2.195   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.916  -0.473   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.396   2.195   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.624   2.195   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.624  -0.473   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.394   0.861   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   13                                                       
CONECT    8    6   14                                                       
CONECT    9   10   11                                                       
CONECT   10    9   12                                                       
CONECT   11    9   15                                                       
CONECT   12   10   16                                                       
CONECT   13    7   15                                                       
CONECT   14    8   17   18                                                  
CONECT   15   11   13                                                       
CONECT   16   12   19                                                       
CONECT   17   14   20                                                       
CONECT   18   14   21                                                       
CONECT   19   16                                                            
CONECT   20    1   17   22                                                  
CONECT   21   18   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
3-[(Z)-8-Pentadecenyl]phenol	Kegg

Chemical Formula

C₂₁H₃₄O

Average Mass

302.5020 Da

Monoisotopic Mass

302.26097 Da

IUPAC Name

3-[(8Z)-pentadec-8-en-1-yl]phenol

Traditional Name

cardanol monoene

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-20-17-15-18-21(22)19-20/h7-8,15,17-19,22H,2-6,9-14,16H2,1H3/b8-7-

InChI Key

YLKVIMNNMLKUGJ-FPLPWBNLSA-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

Species Name	Source	Reference
Anacardium occidentale	LOTUS Database	35616633
Ginkgo biloba	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:146 )

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
logP	8.76	ALOGPS
logP	8.05	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	98.61 m³·mol⁻¹	ChemAxon
Polarizability	39.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002643

Chemspider ID

Not Available

KEGG Compound ID

C10785

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281854

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for cardanol monoene (NP0254772)

MOL for NP0254772 (cardanol monoene)

3D MOL for NP0254772 (cardanol monoene)

3D SDF for NP0254772 (cardanol monoene)

3D-SDF for NP0254772 (cardanol monoene)

PDB for NP0254772 (cardanol monoene)

3D PDB for NP0254772 (cardanol monoene)

SMILES for NP0254772 (cardanol monoene)

INCHI for NP0254772 (cardanol monoene)

Structure for NP0254772 (cardanol monoene)

3D Structure for NP0254772 (cardanol monoene)