NP-MRD: Showing NP-Card for Guaiacin (NP0047888)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:36 UTC

Updated at

2022-03-17 20:47:36 UTC

NP-MRD ID

NP0047888

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Guaiacin

Description

Guaiacin belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. Guaiacin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Guaiacin has been detected, but not quantified in, herbs and spices and ucuhuba. Guaiacin is found in Calyptranthes pallens, Cinnamomum philippinense, Iryanthera juruensis , Machilus robusta, Machilus thunbergii , Machilus wangchiana, Magnolia kachirachirai, Myristica fragrans , Saururus cernuus and Virola carinata. This could make guaiacin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307382D          

 24 26  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    4.2868    0.8250    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  7  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  2  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17 10  1  0  0  0  0
 18  8  1  0  0  0  0
 18 16  2  0  0  0  0
 19  9  1  0  0  0  0
 19 17  2  0  0  0  0
 20 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  3  1  0  0  0  0
 23 18  1  0  0  0  0
 24  4  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047888

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C1

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

> <INCHI_KEY>
TZAAYUCUPIYQBR-UHFFFAOYSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.4022

> <EXACT_MASS>
328.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.379048696776806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.497888109

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.473043833368424

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.849501976916102

> <JCHEM_PKA_STRONGEST_BASIC>
-4.58852653166971

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
94.16919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+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  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5    6   13                                                       
CONECT    6    5   16                                                       
CONECT    7   11   14                                                       
CONECT    8   13   18                                                       
CONECT    9   14   19                                                       
CONECT   10   15   17                                                       
CONECT   11    1    7   12                                                  
CONECT   12    2   11   20                                                  
CONECT   13    5    8   20                                                  
CONECT   14    7    9   15                                                  
CONECT   15   10   14   20                                                  
CONECT   16    6   18   21                                                  
CONECT   17   10   19   22                                                  
CONECT   18    8   16   23                                                  
CONECT   19    9   17   24                                                  
CONECT   20   12   13   15                                                  
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23    3   18                                                       
CONECT   24    4   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(+)-Guaiacin	HMDB
4,4'-Dihydroxy-3',5-dimethoxy-2,7'-cyclolignan	HMDB
5,6,7,8-Tetrahydro-8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-2-naphthalenol, 9ci	HMDB

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4022 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Traditional Name

8-(4-hydroxy-3-methoxyphenyl)-3-methoxy-6,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-ol

CAS Registry Number

36531-08-5

SMILES

COC1=C(O)C=C2C(C(C)C(C)CC2=C1)C1=CC(OC)=C(O)C=C1

InChI Identifier

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

InChI Key

TZAAYUCUPIYQBR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Calyptranthes pallens	LOTUS Database	35616633
Cinnamomum philippinense	Plant	KNApSAcK
Iryanthera juruensis	Plant	KNApSAcK
Machilus robusta	LOTUS Database	35616633
Machilus thunbergii	Plant	KNApSAcK
Machilus wangchiana	Plant	KNApSAcK
Magnolia kachirachirai	LOTUS Database	35616633
Myristica fragrans	Plant	KNApSAcK
Saururus cernuus	LOTUS Database	35616633
Virola carinata	Plant	KNApSAcK
Virola surinamensis	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
Methoxyphenol
Tetralin
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.08	ALOGPS
logP	4.5	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.85	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	3	ChemAxon
Refractivity	94.17 m³·mol⁻¹	ChemAxon
Polarizability	36.38 Å³	ChemAxon
Number of Rings	3	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

HMDB0034178

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012470

KNApSAcK ID

C00037221

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14681584

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Guaiacin (NP0047888)

MOL for NP0047888 (Guaiacin)

3D MOL for NP0047888 (Guaiacin)

3D SDF for NP0047888 (Guaiacin)

3D-SDF for NP0047888 (Guaiacin)

PDB for NP0047888 (Guaiacin)

3D PDB for NP0047888 (Guaiacin)

SMILES for NP0047888 (Guaiacin)

INCHI for NP0047888 (Guaiacin)

Structure for NP0047888 (Guaiacin)

3D Structure for NP0047888 (Guaiacin)