NP-MRD: Showing NP-Card for (+)-(7s,8s)-guaiacylglycerol (NP0324183)

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Record Information

Version

2.0

Created at

2022-09-12 04:06:01 UTC

Updated at

2022-09-12 04:06:01 UTC

NP-MRD ID

NP0324183

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(7s,8s)-guaiacylglycerol

Description

(+)-(7S,8S)-guaiacylglycerol belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety (+)-(7S,8S)-guaiacylglycerol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (+)-(7s,8s)-guaiacylglycerol is found in Bambusa emeiensis, Juniperus communis, Miliusa balansae, Soymida febrifuga and Tarenna attenuata. Based on a literature review very few articles have been published on (+)-(7S,8S)-guaiacylglycerol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.7216    1.5636   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6702    0.2689   -0.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258   -0.3389    0.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619    0.2598   -0.3906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0173   -0.3342   -0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2219    0.3238   -0.7401 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9904   -0.5808   -1.4658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.8238    0.4202 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4526   -0.1864    1.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089    1.4617   -0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0562    0.5250   -0.8767 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0243   -1.5994    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448   -2.2220    0.6703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3671   -1.5968    0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5164   -2.2651    0.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3070    2.2771    0.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1400    1.5606   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7507    1.8640   -0.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804    1.2536   -0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9475    1.1917   -1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5466   -1.4457   -1.5055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087    1.5877    0.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0279   -0.8518    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9694    1.8123    0.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0515    2.3285   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9786    0.8524   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9724   -2.1322    0.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0635   -3.2085    1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4444   -3.1928    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 14  3  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
  6 20  1  6
  7 21  1  0
  8 22  1  1
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
M  END


  Mrv1652309122206062D          

 15 15  0  0  1  0            999 V2000
    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
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    4.2868   -0.0000    0.0000 O   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
    0.0000    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324183

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@H](O)[C@@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O5/c1-15-9-4-6(2-3-7(9)12)10(14)8(13)5-11/h2-4,8,10-14H,5H2,1H3/t8-,10-/m0/s1

> <INCHI_KEY>
LSKFUSLVUZISST-WPRPVWTQSA-N

> <FORMULA>
C10H14O5

> <MOLECULAR_WEIGHT>
214.217

> <EXACT_MASS>
214.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.336807855121897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S)-1-(4-hydroxy-3-methoxyphenyl)propane-1,2,3-triol

> <JCHEM_LOGP>
-0.5160104226666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.122317349679907

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.9085792201856

> <JCHEM_PKA_STRONGEST_BASIC>
-2.977302392601321

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
53.243

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S)-1-(4-hydroxy-3-methoxyphenyl)propane-1,2,3-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄O₅

Average Mass

214.2170 Da

Monoisotopic Mass

214.08412 Da

IUPAC Name

(1S,2S)-1-(4-hydroxy-3-methoxyphenyl)propane-1,2,3-triol

Traditional Name

(1S,2S)-1-(4-hydroxy-3-methoxyphenyl)propane-1,2,3-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@H](O)[C@@H](O)CO

InChI Identifier

InChI=1S/C10H14O5/c1-15-9-4-6(2-3-7(9)12)10(14)8(13)5-11/h2-4,8,10-14H,5H2,1H3/t8-,10-/m0/s1

InChI Key

LSKFUSLVUZISST-WPRPVWTQSA-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
Bambusa emeiensis	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Miliusa balansae	LOTUS Database	35616633
Soymida febrifuga	LOTUS Database	35616633
Tarenna attenuata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Sugar alcohol
Secondary alcohol
Ether
Polyol
Primary alcohol
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

guaiacylglycerol (CHEBI:67646 )

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	-0.52	ChemAxon
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.24 m³·mol⁻¹	ChemAxon
Polarizability	21.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

10193232

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12310249

PDB ID

Not Available

ChEBI ID

67646

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (+)-(7s,8s)-guaiacylglycerol (NP0324183)

MOL for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)

3D MOL for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)

3D SDF for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)

3D-SDF for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)

PDB for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)

3D PDB for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)

SMILES for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)

INCHI for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)

Structure for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)

3D Structure for NP0324183 ((+)-(7s,8s)-guaiacylglycerol)