NP-MRD: Showing NP-Card for Guaiaretic acid (NP0050415)

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Record Information

Version

2.0

Created at

2022-04-27 21:35:52 UTC

Updated at

2022-04-27 21:35:52 UTC

NP-MRD ID

NP0050415

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Guaiaretic acid

Description

(?)-Guaiaretic acid, also known as (?)-Guaiaretate, belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Guaiaretic acid is found in Guaiacum officinale . Guaiaretic acid was first documented in 2009 (PMID: 21583141). Based on a literature review a small amount of articles have been published on (?)-Guaiaretic acid (PMID: 23915010) (PMID: 20000780).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223352D          

 24 25  0  0  1  0            999 V2000
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    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
   -1.4289   -4.1250    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  2  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
   -5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -6.1875    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
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9500    0.0000 O   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
   -7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  0  0  0  0
  8 21  1  6  0  0  0
  2 22  1  0  0  0  0
  1 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050415

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C(/C)[C@H](C)CC2=CC(OC)=C(O)C=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-9,11-12,14,21-22H,10H2,1-4H3/b13-9+/t14-/m1/s1

> <INCHI_KEY>
OPAORDVBZRVVNQ-KADHNRKRSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.408

> <EXACT_MASS>
328.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.23447225601626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2R,3E)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbut-3-en-1-yl]-2-methoxyphenol

> <ALOGPS_LOGP>
4.46

> <JCHEM_LOGP>
4.727431374666667

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.44521372200029

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.800354391812869

> <JCHEM_PKA_STRONGEST_BASIC>
-4.591462035577327

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
96.43360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2R,3E)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbut-3-en-1-yl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334 -10.010   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      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2    6   23                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14                                                            
CONECT   20    9                                                            
CONECT   21    8                                                            
CONECT   22    2                                                            
CONECT   23    1   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
(?)-guaiaretate	Generator

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4080 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

4-[(2R,3E)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbut-3-en-1-yl]-2-methoxyphenol

Traditional Name

4-[(2R,3E)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbut-3-en-1-yl]-2-methoxyphenol

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C(/C)[C@H](C)CC2=CC(OC)=C(O)C=C2)=CC=C1O

InChI Identifier

InChI=1S/C20H24O4/c1-13(9-15-5-7-17(21)19(11-15)23-3)14(2)10-16-6-8-18(22)20(12-16)24-4/h5-9,11-12,14,21-22H,10H2,1-4H3/b13-9+/t14-/m1/s1

InChI Key

OPAORDVBZRVVNQ-KADHNRKRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Guaiacum officinale	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Norlignan skeleton
Methoxyphenol
Phenylpropane
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
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	4.46	ALOGPS
logP	4.73	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	96.43 m³·mol⁻¹	ChemAxon
Polarizability	37.23 Å³	ChemAxon
Number of Rings	2	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

114928767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

90473890

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hermann PM, Park D, Beaulieu E, Wildering WC: Evidence for inflammation-mediated memory dysfunction in gastropods: putative PLA2 and COX inhibitors abolish long-term memory failure induced by systemic immune challenges. BMC Neurosci. 2013 Aug 6;14:83. doi: 10.1186/1471-2202-14-83. [PubMed:23915010 ]
Wen J, Shi H, Xu Z, Chang H, Jia C, Zan K, Jiang Y, Tu P: Dimeric guaianolides and sesquiterpenoids from Artemisia anomala. J Nat Prod. 2010 Jan;73(1):67-70. doi: 10.1021/np900462u. [PubMed:20000780 ]
Salinas-Salazar CL, Del Rayo Camacho-Corona M, Bernes S, Waksman de Torres N: 2,2'-Dimethoxy-4,4'-[rel-(2R,3S)-2,3-di-methylbutane-1,4-diyl]diphenol. Acta Crystallogr Sect E Struct Rep Online. 2009 May 14;65(Pt 6):o1279. doi: 10.1107/S1600536809017292. [PubMed:21583141 ]

Showing NP-Card for Guaiaretic acid (NP0050415)

MOL for NP0050415 (Guaiaretic acid)

3D MOL for NP0050415 (Guaiaretic acid)

3D SDF for NP0050415 (Guaiaretic acid)

3D-SDF for NP0050415 (Guaiaretic acid)

PDB for NP0050415 (Guaiaretic acid)

3D PDB for NP0050415 (Guaiaretic acid)

SMILES for NP0050415 (Guaiaretic acid)

INCHI for NP0050415 (Guaiaretic acid)

Structure for NP0050415 (Guaiaretic acid)

3D Structure for NP0050415 (Guaiaretic acid)