NP-MRD: Showing NP-Card for Pawhuskin A (NP0026874)

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Record Information

Version

2.0

Created at

2021-06-19 18:39:14 UTC

Updated at

2021-06-29 23:52:40 UTC

NP-MRD ID

NP0026874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pawhuskin A

Provided By

JEOL Database JEOL Logo

Description

Pawhuskin A is found in Dalea purpurea. Pawhuskin A was first documented in 2004 (PMID: 14738380). Based on a literature review a small amount of articles have been published on Pawhuskin A (PMID: 26771823) (PMID: 26525865) (PMID: 24456556) (PMID: 18922035).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120393D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192120393D          

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M  END
> <DATABASE_ID>
NP0026874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C(C(\C([H])=C(/[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])=C1[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O4/c1-19(2)7-6-8-21(5)10-15-25-23(17-24(30)18-28(25)32)12-11-22-13-16-27(31)29(33)26(22)14-9-20(3)4/h7,9-13,16-18,30-33H,6,8,14-15H2,1-5H3/b12-11+,21-10+

> <INCHI_KEY>
LZRXMBPDNILKDO-ZVBRSKEYSA-N

> <FORMULA>
C29H36O4

> <MOLECULAR_WEIGHT>
448.603

> <EXACT_MASS>
448.261359639

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.224502581746265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(E)-2-[3,4-dihydroxy-2-(3-methylbut-2-en-1-yl)phenyl]ethenyl]-4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]benzene-1,3-diol

> <ALOGPS_LOGP>
6.26

> <JCHEM_LOGP>
8.21567383833333

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.871342772444097

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.282588420383254

> <JCHEM_PKA_STRONGEST_BASIC>
-6.179563327168464

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
141.7246

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pawhuskin A

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.681  -1.775  -0.502  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.749  -0.385  -1.071  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.962   0.690  -0.037  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.626  -0.061  -2.374  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.390  -0.974  -3.548  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.152  -0.580  -4.373  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.162  -0.672  -3.614  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.599  -2.065  -3.256  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.854   0.450  -3.324  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.136   0.588  -2.543  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.026   1.632  -1.444  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.409   2.962  -1.698  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.891   3.291  -2.936  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.302   3.952  -0.722  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.794   3.621   0.525  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.687   4.615   1.453  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.399   2.320   0.810  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.517   1.314  -0.164  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.052  -0.040   0.171  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.504  -0.729   1.231  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.001  -2.071   1.556  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.129  -3.086   0.586  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.655  -4.377   0.820  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.054  -4.655   2.037  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.561  -5.898   2.329  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.935  -3.666   3.015  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.330  -4.003   4.198  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.412  -2.364   2.807  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.263  -1.318   3.897  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.114  -0.372   3.657  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.031   0.921   4.030  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.081   1.660   4.813  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.189   1.740   3.697  0.00  0.00           C+0
HETATM   34  H   UNK     0       1.449  -2.542  -1.242  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.640  -2.038  -0.044  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.909  -1.827   0.272  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.025   1.689  -0.480  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.131   0.696   0.676  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.892   0.510   0.512  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.697   0.993  -2.646  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.269  -0.907  -4.201  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.315  -2.024  -3.253  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.297   0.434  -4.768  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.091  -1.231  -5.254  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.635  -2.118  -2.915  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.963  -2.474  -2.466  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.525  -2.720  -4.131  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.450   1.405  -3.663  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.938   0.860  -3.240  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.465  -0.358  -2.101  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.102   4.239  -2.947  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.598   4.977  -0.918  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.297   4.241   2.260  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.982   2.074   1.783  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.300  -0.455  -0.495  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.250  -0.315   1.903  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.605  -2.866  -0.368  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.764  -5.134   0.051  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.722  -6.474   1.562  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.089  -4.946   4.092  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.106  -1.806   4.866  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.215  -0.787   3.994  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.730  -0.812   3.125  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.920   1.029   5.115  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.644   2.072   5.729  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.481   2.489   4.221  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.912   2.589   3.064  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.947   1.158   3.163  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.651   2.123   4.613  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   37   38   39                                             
CONECT    4    5    2   40                                                  
CONECT    5    6    4   41   42                                             
CONECT    6    7    5   43   44                                             
CONECT    7    9    6    8                                                  
CONECT    8    7   45   46   47                                             
CONECT    9   10    7   48                                                  
CONECT   10   11    9   49   50                                             
CONECT   11   12   18   10                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12   51                                                       
CONECT   14   15   12   52                                                  
CONECT   15   17   14   16                                                  
CONECT   16   15   53                                                       
CONECT   17   18   15   54                                                  
CONECT   18   17   11   19                                                  
CONECT   19   20   18   55                                                  
CONECT   20   21   19   56                                                  
CONECT   21   22   20   28                                                  
CONECT   22   21   23   57                                                  
CONECT   23   22   24   58                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   59                                                       
CONECT   26   28   27   24                                                  
CONECT   27   26   60                                                       
CONECT   28   26   29   21                                                  
CONECT   29   30   28   61   62                                             
CONECT   30   29   31   63                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   64   65   66                                             
CONECT   33   31   67   68   69                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    6                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47    8                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   10                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   16                                                            
CONECT   54   17                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   22                                                            
CONECT   58   23                                                            
CONECT   59   25                                                            
CONECT   60   27                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   32                                                            
CONECT   65   32                                                            
CONECT   66   32                                                            
CONECT   67   33                                                            
CONECT   68   33                                                            
CONECT   69   33                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  140    0
END

RDKit          3D

69 70  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₄

Average Mass

448.6030 Da

Monoisotopic Mass

448.26136 Da

IUPAC Name

5-[(E)-2-[3,4-dihydroxy-2-(3-methylbut-2-en-1-yl)phenyl]ethenyl]-4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]benzene-1,3-diol

Traditional Name

pawhuskin A

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C(C(\C([H])=C(/[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])=C1[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C29H36O4/c1-19(2)7-6-8-21(5)10-15-25-23(17-24(30)18-28(25)32)12-11-22-13-16-27(31)29(33)26(22)14-9-20(3)4/h7,9-13,16-18,30-33H,6,8,14-15H2,1-5H3/b12-11+,21-10+

InChI Key

LZRXMBPDNILKDO-ZVBRSKEYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dalea purpurea	JEOL database	Belofsky, G., et al, J. Nat. Prod. 67, 26 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Catechol
Resorcinol
Styrene
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Organooxygen compound
Organic oxygen compound
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	6.26	ALOGPS
logP	8.22	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	8.28	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	141.72 m³·mol⁻¹	ChemAxon
Polarizability	51.22 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

Not Available

Chemspider ID

8541870

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pawhuskin A

METLIN ID

Not Available

PubChem Compound

10366422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gardner KD, Wiemer DF: Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues. J Org Chem. 2016 Feb 19;81(4):1585-92. doi: 10.1021/acs.joc.5b02756. Epub 2016 Jan 28. [PubMed:26771823 ]
Belofsky G, French AN, Wallace DR, Dodson SL: New geranyl stilbenes from Dalea purpurea with in vitro opioid receptor affinity. J Nat Prod. 2004 Jan;67(1):26-30. doi: 10.1021/np030258d. [PubMed:14738380 ]
Hartung AM, Navarro HA, Wiemer DF, Neighbors JD: A selective delta opioid receptor antagonist based on a stilbene core. Bioorg Med Chem Lett. 2015 Dec 1;25(23):5532-5. doi: 10.1016/j.bmcl.2015.10.059. Epub 2015 Oct 23. [PubMed:26525865 ]
Hartung AM, Beutler JA, Navarro HA, Wiemer DF, Neighbors JD: Stilbenes as kappa-selective, non-nitrogenous opioid receptor antagonists. J Nat Prod. 2014 Feb 28;77(2):311-9. doi: 10.1021/np4009046. Epub 2014 Jan 23. [PubMed:24456556 ]
Neighbors JD, Buller MJ, Boss KD, Wiemer DF: A concise synthesis of pawhuskin A. J Nat Prod. 2008 Nov;71(11):1949-52. doi: 10.1021/np800351c. Epub 2008 Oct 15. [PubMed:18922035 ]
Belofsky, G., et al. (2004). Belofsky, G., et al, J. Nat. Prod. 67, 26 (2004). J. Nat. Prod..

Showing NP-Card for Pawhuskin A (NP0026874)

MOL for NP0026874 (Pawhuskin A)

3D MOL for NP0026874 (Pawhuskin A)

3D SDF for NP0026874 (Pawhuskin A)

3D-SDF for NP0026874 (Pawhuskin A)

PDB for NP0026874 (Pawhuskin A)

3D PDB for NP0026874 (Pawhuskin A)

SMILES for NP0026874 (Pawhuskin A)

INCHI for NP0026874 (Pawhuskin A)

Structure for NP0026874 (Pawhuskin A)

3D Structure for NP0026874 (Pawhuskin A)