NP-MRD: Showing NP-Card for 4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid (NP0307627)

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Record Information

Version

2.0

Created at

2022-09-11 00:52:57 UTC

Updated at

2022-09-11 00:52:57 UTC

NP-MRD ID

NP0307627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid

Description

CHEMBL238753 belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. 4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid is found in Piper crassinervium. Based on a literature review very few articles have been published on CHEMBL238753.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
   -6.2275    0.6674   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2037    0.6522    0.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4517    1.4328    2.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0712   -0.0479    0.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7856   -0.8359   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6309   -0.3347   -1.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3644   -0.3148   -0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1072    0.5790    0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3255   -1.0756   -0.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417   -1.0648   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9439   -0.6310   -1.0847 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -0.5368   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5981   -0.8379    0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9079   -0.7299    1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082   -0.3203    0.2505 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3071   -0.2051    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5480   -0.4981    1.9035 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3159    0.2004   -0.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -0.0196   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2450   -0.1243   -1.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863    0.1805   -2.7990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9824    1.4622   -0.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7486   -0.3103   -0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7731    0.8293   -1.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4729    1.2254    2.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4195    2.5207    1.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7457    1.1793    2.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3819   -0.0431    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6366   -1.9099   -0.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7195   -0.9102   -1.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8155    0.6999   -1.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253   -0.9470   -2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    1.1317    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8591    1.4215    0.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0446    0.1027    1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4240   -1.7071   -1.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370   -2.1310    0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722   -0.4703    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7971   -1.1630    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1305   -0.9771    2.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4270    1.2107   -0.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3177    0.3071   -1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5659    0.4849   -3.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 19  1  0
 19 20  2  0
 20 21  1  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
 20 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 13 39  1  0
 14 40  1  0
 19 42  1  0
 21 43  1  0
 18 41  1  0
M  END


  Mrv1652309112202522D          

 21 21  0  0  0  0            999 V2000
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    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
    0.7145    4.5375    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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
    0.7145   -0.4125    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0307627

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\COC1=CC=C(C=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-12(2)5-4-6-13(3)9-10-21-16-8-7-14(17(19)20)11-15(16)18/h5,7-9,11,18H,4,6,10H2,1-3H3,(H,19,20)/b13-9+

> <INCHI_KEY>
WSNILKGNSNUWSJ-UKTHLTGXSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.359

> <EXACT_MASS>
290.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.92415670146071

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid

> <JCHEM_LOGP>
4.190552501333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.926930848338396

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.138410991305774

> <JCHEM_PKA_STRONGEST_BASIC>
-4.946674975166919

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
84.67909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15   20                                                       
CONECT   20   19   12   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂O₄

Average Mass

290.3590 Da

Monoisotopic Mass

290.15181 Da

IUPAC Name

4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid

Traditional Name

4-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\COC1=CC=C(C=C1O)C(O)=O

InChI Identifier

InChI=1S/C17H22O4/c1-12(2)5-4-6-13(3)9-10-21-16-8-7-14(17(19)20)11-15(16)18/h5,7-9,11,18H,4,6,10H2,1-3H3,(H,19,20)/b13-9+

InChI Key

WSNILKGNSNUWSJ-UKTHLTGXSA-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
Piper crassinervium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Aromatic monoterpenoid
Hydroxybenzoic acid
Monocyclic monoterpenoid
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Phenol ether
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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
logP	4.19	ChemAxon
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	84.68 m³·mol⁻¹	ChemAxon
Polarizability	32.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

23303823

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44439603

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid (NP0307627)

MOL for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)

3D MOL for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)

3D SDF for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)

3D-SDF for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)

PDB for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)

3D PDB for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)

SMILES for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)

INCHI for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)

Structure for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)

3D Structure for NP0307627 (4-{[(2e)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-3-hydroxybenzoic acid)