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Showing NP-Card for sequoyitol (NP0165657)

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Record Information
Version2.0
Created at2022-09-03 00:51:43 UTC
Updated at2022-09-03 00:51:43 UTC
NP-MRD IDNP0165657
Secondary Accession NumbersNone
Natural Product Identification
Common Namesequoyitol
DescriptionSequoyitol belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Sequoyitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Sequoyitol has been detected, but not quantified in, ginkgo nuts and soy beans. sequoyitol is found in Amentotaxus yunnanensis, Macrozamia riedlei and Melicope micrococca. sequoyitol was first documented in 2003 (PMID: 12880325). This could make sequoyitol a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0165657 (sequoyitol)

 
  Mrv0541 02241221162D          

 13 13  0  0  1  0            999 V2000
   10.4313   -9.3743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0223   -8.6575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2563   -9.3743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0214  -10.0790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4381   -7.9406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2088   -8.6552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6695   -8.6677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6221  -10.0074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2604   -7.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0380   -7.2317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4847   -8.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6721   -7.2494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4316  -10.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  3  7  1  0  0  0  0
  3  8  1  6  0  0  0
  5  9  1  0  0  0  0
  5 10  1  1  0  0  0
  7 11  1  1  0  0  0
  9 12  1  1  0  0  0
  7  9  1  0  0  0  0
  4 13  1  0  0  0  0
M  END
Download

3D MOL for NP0165657 (sequoyitol)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
    2.4626   -1.3449    1.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0995   -1.1640    1.4170 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164   -0.2951    0.3577 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1689    0.9219    0.9293 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9694    2.0757    0.7528 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2282    1.1662    0.3905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0225    0.1178    0.8545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784    1.1278   -1.1105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4489    1.4818   -1.5947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291   -0.2438   -1.5508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0413   -0.9416   -1.7647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005   -1.0419   -0.6335 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9014   -1.8060   -1.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -1.7766    0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9303   -0.4028    1.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5852   -2.0716    2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8060    0.0202   -0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0403    0.8530    2.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    1.8318    0.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5661    2.1489    0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230   -0.0929    1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4753    1.8910   -1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394    2.4355   -1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712   -0.1730   -2.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597   -0.3609   -2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6084   -1.8208   -0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419   -2.5358   -0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  6
  4 18  1  1
  5 19  1  0
  6 20  1  6
  7 21  1  0
  8 22  1  6
  9 23  1  0
 10 24  1  6
 11 25  1  0
 12 26  1  1
 13 27  1  0
M  END
Download

3D SDF for NP0165657 (sequoyitol)

 
  Mrv0541 02241221162D          

 13 13  0  0  1  0            999 V2000
   10.4313   -9.3743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0223   -8.6575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2563   -9.3743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0214  -10.0790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4381   -7.9406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2088   -8.6552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6695   -8.6677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6221  -10.0074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2604   -7.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0380   -7.2317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4847   -8.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6721   -7.2494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4316  -10.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  3  7  1  0  0  0  0
  3  8  1  6  0  0  0
  5  9  1  0  0  0  0
  5 10  1  1  0  0  0
  7 11  1  1  0  0  0
  9 12  1  1  0  0  0
  7  9  1  0  0  0  0
  4 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165657

> <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+

> <INCHI_KEY>
DSCFFEYYQKSRSV-GWJPIIGYSA-N

> <FORMULA>
C7H14O6

> <MOLECULAR_WEIGHT>
194.1825

> <EXACT_MASS>
194.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
17.990246868718227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3r,4R,5S,6r)-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>
sequoyitol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0165657 (sequoyitol)

Download
PDB for NP0165657 (sequoyitol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      19.472 -17.499   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.708 -16.161   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.012 -17.499   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      18.707 -18.814   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      19.484 -14.822   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      17.190 -16.156   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      21.783 -16.180   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      21.695 -18.680   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      21.019 -14.842   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      18.738 -13.499   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      23.305 -16.190   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      21.788 -13.532   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.472 -20.150   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1   13                                                       
CONECT    5    2    9   10                                                  
CONECT    6    2                                                            
CONECT    7    3   11    9                                                  
CONECT    8    3                                                            
CONECT    9    5   12    7                                                  
CONECT   10    5                                                            
CONECT   11    7                                                            
CONECT   12    9                                                            
CONECT   13    4                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

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3D PDB for NP0165657 (sequoyitol)
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SMILES for NP0165657 (sequoyitol)
CO[C@@H]1[C@@H](O)[C@H](O)[C@H](O)[C@H](O)[C@H]1O
Download
INCHI for NP0165657 (sequoyitol)
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+
Download
View in JSmol
Synonyms
ValueSource
(1R,2S,3R,4R,5S,6R)-6-Methoxycyclohexane-1,2,3,4,5-pentolChEBI
5-O-Methyl-myo-inositolChEBI
1D-5-O-Methyl-myo-inositolKegg
SequoyitolChEBI
Chemical FormulaC7H14O6
Average Mass194.1825 Da
Monoisotopic Mass194.07904 Da
IUPAC Name(1R,2S,3r,4R,5S,6r)-6-methoxycyclohexane-1,2,3,4,5-pentol
Traditional Namesequoyitol
CAS Registry NumberNot 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+
InChI KeyDSCFFEYYQKSRSV-GWJPIIGYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Amentotaxus yunnanensisLOTUS Database
Macrozamia riedleiLOTUS Database
Melicope micrococcaLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentCyclohexanols  
Alternative Parents
Substituents
  • Cyclohexanol
    • 

  • Cyclitol or derivatives
    • 

  • Cyclic alcohol
    • 

  • Polyol
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.7ALOGPS
logP-3.1ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.53 m³·mol⁻¹ChemAxon
Polarizability17.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031449  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005616  
KNApSAcK IDC00001172  
Chemspider ID10197144  
KEGG Compound IDC03365  
BioCyc ID5-O-METHYL-MYO-INOSITOL  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15975  
Good Scents IDNot Available
References
General References
  1. Li SH, Zhang HJ, Niu XM, Yao P, Sun HD, Fong HH: Chemical constituents from Amentotaxus yunnanensis and Torreyayunnanensis. J Nat Prod. 2003 Jul;66(7):1002-5. doi: 10.1021/np030117b. [PubMed:12880325  ] 
  2. LOTUS database [Link]