NP-MRD: Showing NP-Card for Mesquitol-4alpha-ol 8-methyl ether (NP0056236)

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Record Information

Version

2.0

Created at

2022-04-28 02:04:14 UTC

Updated at

2022-04-28 02:04:14 UTC

NP-MRD ID

NP0056236

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mesquitol-4alpha-ol 8-methyl ether

Description

Mesquitol-4alpha-ol 8-methyl ether belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions. Thus, mesquitol-4alpha-ol 8-methyl ether is considered to be a flavonoid. Mesquitol-4alpha-ol 8-methyl ether is found in Acacia saxatilis. Based on a literature review very few articles have been published on Mesquitol-4alpha-ol 8-methyl ether.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    1.6186   -2.9710   -0.8948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2890   -2.3124    0.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6219   -0.9779   -0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8466   -0.6766   -0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7207   -1.6863   -0.9384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1540    0.6638   -0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542    1.6380   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0230    1.3287    0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173   -0.0066    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5093   -0.3458    0.9189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505    0.5609    1.1358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7638   -0.0409    0.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271   -0.5893   -0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7134   -1.1593   -1.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9242   -1.1503   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0260   -1.7211   -1.2654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0522   -0.6072    0.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2970   -0.6354    1.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -0.0341    1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3188    1.8914    0.4674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2366    2.8121    0.9630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703    2.4073    0.6078 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2524    3.4973   -0.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4608   -2.2931   -1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597   -3.4021   -0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075   -3.7705   -1.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4360   -2.6434   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128    0.9095   -1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4706    2.6902   -0.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6645    0.6919    2.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6820   -0.5706   -1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -1.5997   -2.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9254   -1.7457   -0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3924   -0.2241    2.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127    0.4036    2.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5398    1.7746   -0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    2.9405    1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2370    2.6847    1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437    4.2692    0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9 10  1  0
 10 11  1  0
 11 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  8  1  0
  8  7  2  0
  7  6  1  0
  6  4  2  0
  4  5  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
  4  3  1  0
 19 12  1  0
  8  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 11 30  1  1
 20 36  1  6
 21 37  1  0
 22 38  1  1
 23 39  1  0
  7 29  1  0
  6 28  1  0
  5 27  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
M  END


  Mrv1652304282204042D          

 23 25  0  0  1  0            999 V2000
   -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
    0.0000   -1.6500    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
    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 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   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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    0.8250    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  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
  4 12  1  0  0  0  0
 12 13  1  6  0  0  0
 11 14  1  1  0  0  0
 10 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056236

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2O[C@@H]([C@@H](O)[C@H](O)C2=CC=C1O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O7/c1-22-16-10(18)5-3-8-12(20)13(21)14(23-15(8)16)7-2-4-9(17)11(19)6-7/h2-6,12-14,17-21H,1H3/t12-,13+,14-/m1/s1

> <INCHI_KEY>
ILQKGSIPOHRREM-HZSPNIEDSA-N

> <FORMULA>
C16H16O7

> <MOLECULAR_WEIGHT>
320.297

> <EXACT_MASS>
320.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
30.506039331943725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-8-methoxy-3,4-dihydro-2H-1-benzopyran-3,4,7-triol

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
1.022004924333333

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.993703159848598

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.129900455781083

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6165703176354604

> <JCHEM_POLAR_SURFACE_AREA>
119.61000000000001

> <JCHEM_REFRACTIVITY>
79.68950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mesquitol-4α-ol 8-methyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   23                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15   10   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19                                                            
CONECT   22   18                                                            
CONECT   23    1                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
Mesquitol-4a-ol 8-methyl ether	Generator
Mesquitol-4α-ol 8-methyl ether	Generator

Chemical Formula

C₁₆H₁₆O₇

Average Mass

320.2970 Da

Monoisotopic Mass

320.08960 Da

IUPAC Name

(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-8-methoxy-3,4-dihydro-2H-1-benzopyran-3,4,7-triol

Traditional Name

mesquitol-4α-ol 8-methyl ether

CAS Registry Number

Not Available

SMILES

COC1=C2O[C@@H]([C@@H](O)[C@H](O)C2=CC=C1O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C16H16O7/c1-22-16-10(18)5-3-8-12(20)13(21)14(23-15(8)16)7-2-4-9(17)11(19)6-7/h2-6,12-14,17-21H,1H3/t12-,13+,14-/m1/s1

InChI Key

ILQKGSIPOHRREM-HZSPNIEDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acacia saxatilis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Leucoanthocyanidins

Alternative Parents

Substituents

8-methoxyflavonoid-skeleton
Leucoanthocyanidin-skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
Hydroxyflavonoid
4-hydroxyflavonoid
7-hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Anisole
Catechol
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
1,2-diol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020194 )

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	0.71	ALOGPS
logP	1.02	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.69 m³·mol⁻¹	ChemAxon
Polarizability	30.51 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00009012

Chemspider ID

24842611

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257149

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Mesquitol-4alpha-ol 8-methyl ether (NP0056236)

MOL for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)

3D MOL for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)

3D SDF for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)

3D-SDF for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)

PDB for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)

3D PDB for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)

SMILES for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)

INCHI for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)

Structure for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)

3D Structure for NP0056236 (Mesquitol-4alpha-ol 8-methyl ether)