NP-MRD: Showing NP-Card for 1d-5-o-methyl-chiro-inositol (NP0242045)

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Record Information

Version

2.0

Created at

2022-09-07 02:15:39 UTC

Updated at

2022-09-07 02:15:39 UTC

NP-MRD ID

NP0242045

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1d-5-o-methyl-chiro-inositol

Description

1D-5-O-methyl-chiro-inositol, also known as matezitol or sennitol, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. A cyclitol ether formed by etherification of the 5-hydroxy group of 1D-chiro-inositol. 1d-5-o-methyl-chiro-inositol is found in Magonia pubescens. 1D-5-O-methyl-chiro-inositol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305061921522D          

 13 13  0  0  0  0            999 V2000
   -0.0625    1.9188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0625    2.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7770    1.5063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4914    1.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    0.2687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0625   -0.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7770    0.6812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4914    0.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520    1.5063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3664    1.9188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520    0.6812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3664    0.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3664   -0.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  9  1  0  0  0  0
  3  7  1  0  0  0  0
  7  5  1  0  0  0  0
  5 11  1  0  0  0  0
 11  9  1  0  0  0  0
  1  2  1  1  0  0  0
  3  4  1  1  0  0  0
  5  6  1  1  0  0  0
  7  8  1  6  0  0  0
  9 10  1  6  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242045

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m1/s1

> <INCHI_KEY>
DSCFFEYYQKSRSV-NYLBLOMBSA-N

> <FORMULA>
C7H14O6

> <MOLECULAR_WEIGHT>
194.183

> <EXACT_MASS>
194.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.153805054234528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4R,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol

> <ALOGPS_LOGP>
-2.67

> <JCHEM_LOGP>
-3.138883148333333

> <ALOGPS_LOGS>
0.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.999964550804691

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.360891065931447

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6457717234067664

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
40.526199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1D-5-O-methyl-chiro-inositol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.117   3.582   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.117   5.122   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.450   2.812   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.784   3.582   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.117   0.502   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.117  -1.038   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.450   1.272   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.784   0.502   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.217   2.812   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.551   3.582   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.217   1.272   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.551   0.502   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.551  -1.038   0.000  0.00  0.00           C+0
CONECT    1    3    9    2                                                  
CONECT    2    1                                                            
CONECT    3    1    7    4                                                  
CONECT    4    3                                                            
CONECT    5    7   11    6                                                  
CONECT    6    5                                                            
CONECT    7    3    5    8                                                  
CONECT    8    7                                                            
CONECT    9    1   11   10                                                  
CONECT   10    9                                                            
CONECT   11    5    9   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3R,4R,5S,6S)-6-Methoxycyclohexane-1,2,3,4,5-pentol	ChEBI
1D-(1,2,4/3,5,6)-5-O-methylcyclohexanehexol	ChEBI
1D-2-O-Methyl-chiro-inositol	ChEBI
Matezitol	ChEBI
Sennitol	ChEBI
2-O-Methyl-chiro-inositol	HMDB
2-O-Methylchiroinositol	HMDB
1D-5-O-Methyl-chiro-inositol	HMDB
2-O-Methyl-D-chiro-inositol	HMDB
Caesalpinitol	HMDB
D-Quebrachitol	HMDB

Chemical Formula

C₇H₁₄O₆

Average Mass

194.1830 Da

Monoisotopic Mass

194.07904 Da

IUPAC Name

(1S,2R,3R,4R,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol

Traditional Name

1D-5-O-methyl-chiro-inositol

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5+,6+,7-/m1/s1

InChI Key

DSCFFEYYQKSRSV-NYLBLOMBSA-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
Magonia pubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclohexanols

Alternative Parents

Substituents

Cyclohexanol
Cyclitol or derivatives
Cyclic alcohol
Polyol
Ether
Dialkyl ether
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

cyclitol ether (CHEBI:18173 )

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	-2.7	ALOGPS
logP	-3.1	ChemAxon
logS	0.45	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.53 m³·mol⁻¹	ChemAxon
Polarizability	18.15 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

HMDB0062564

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001168

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

Not Available

PDB ID

Not Available

ChEBI ID

18173

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1d-5-o-methyl-chiro-inositol (NP0242045)

MOL for NP0242045 (1d-5-o-methyl-chiro-inositol)

3D MOL for NP0242045 (1d-5-o-methyl-chiro-inositol)

3D SDF for NP0242045 (1d-5-o-methyl-chiro-inositol)

3D-SDF for NP0242045 (1d-5-o-methyl-chiro-inositol)

PDB for NP0242045 (1d-5-o-methyl-chiro-inositol)

3D PDB for NP0242045 (1d-5-o-methyl-chiro-inositol)

SMILES for NP0242045 (1d-5-o-methyl-chiro-inositol)

INCHI for NP0242045 (1d-5-o-methyl-chiro-inositol)

Structure for NP0242045 (1d-5-o-methyl-chiro-inositol)

3D Structure for NP0242045 (1d-5-o-methyl-chiro-inositol)