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Showing NP-Card for Cycloalliin (NP0045362)

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Record Information
Version2.0
Created at2022-03-17 19:18:38 UTC
Updated at2022-03-17 19:18:38 UTC
NP-MRD IDNP0045362
Secondary Accession NumbersNone
Natural Product Identification
Common NameCycloalliin
Description2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one has been detected, but not quantified in, flaxseeds. This could make 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045362 (Cycloalliin)


  Mrv0541 05061304462D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    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
    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    0.0000    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    0.8250    0.0000 N   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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11 10  2  0  0  0  0
M  END
Download

3D MOL for NP0045362 (Cycloalliin)

     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.3747   -1.2679   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -0.2760    0.2772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5395    0.9596   -0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2314    2.1969   -0.2741 S   0  0  0  0  0  4  0  0  0  0  0  0
    0.3492    2.4932   -1.6686 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659    1.2588    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0889   -0.0759   -0.1553 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3659   -0.7726    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3145   -1.9601    0.5267 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -0.1189   -0.0853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0311   -0.8895    0.1027 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7986   -1.0434   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607   -2.3105   -0.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1606   -1.3379    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4694   -0.0051    1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7548    0.7951   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667    1.4381   -0.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934    1.1126    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.7449    0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726    0.2070   -1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959   -0.5264    0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106   -1.6220    0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  6
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7 11  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  1
  3 16  1  0
  3 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  6
 11 22  1  0
 10 21  1  0
M  END
Download

3D SDF for NP0045362 (Cycloalliin)


  Mrv0541 05061304462D          

 11 11  0  0  0  0            999 V2000
    0.7145    2.0625    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
    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    0.0000    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    0.8250    0.0000 N   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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045362

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CS(=O)CC(N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3S/c1-4-2-11(10)3-5(7-4)6(8)9/h4-5,7H,2-3H2,1H3,(H,8,9)

> <INCHI_KEY>
JYMHODZXTIGVPA-UHFFFAOYSA-N

> <FORMULA>
C6H11NO3S

> <MOLECULAR_WEIGHT>
177.221

> <EXACT_MASS>
177.045963913

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.068446884592248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylic acid

> <ALOGPS_LOGP>
-1.91

> <JCHEM_LOGP>
-3.9961933820674522

> <ALOGPS_LOGS>
-0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2595480847291571

> <JCHEM_PKA_STRONGEST_BASIC>
7.78928547050312

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
41.8947

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0045362 (Cycloalliin)

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PDB for NP0045362 (Cycloalliin)
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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0       2.667   0.000   0.000  0.00  0.00           S+0
CONECT    1    4                                                            
CONECT    2    4   11                                                       
CONECT    3    5   11                                                       
CONECT    4    1    2    7                                                  
CONECT    5    3    6    7                                                  
CONECT    6    5    8    9                                                  
CONECT    7    4    5                                                       
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10   11                                                            
CONECT   11    2    3   10                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0045362 (Cycloalliin)
Download
SMILES for NP0045362 (Cycloalliin)
CC1CS(=O)CC(N1)C(O)=O
Download
INCHI for NP0045362 (Cycloalliin)
InChI=1S/C6H11NO3S/c1-4-2-11(10)3-5(7-4)6(8)9/h4-5,7H,2-3H2,1H3,(H,8,9)
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View in JSmol
Synonyms
ValueSource
3-Methyl-1,4-thiazane-5-carboxylic acid-1-oxideHMDB
5-Methyl-3-thiomorpholinecarboxylic acid 1-oxide, 9ciHMDB
CycloallinHMDB
5-Methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylateGenerator
CycloalliinMeSH
Chemical FormulaC6H11NO3S
Average Mass177.2210 Da
Monoisotopic Mass177.04596 Da
IUPAC Name5-methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylic acid
Traditional Name5-methyl-1-oxo-1λ⁴-thiomorpholine-3-carboxylic acid
CAS Registry Number455-41-4
SMILES
CC1CS(=O)CC(N1)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3S/c1-4-2-11(10)3-5(7-4)6(8)9/h4-5,7H,2-3H2,1H3,(H,8,9)
InChI KeyJYMHODZXTIGVPA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium ampeloprasumFooDB
Allium cepaFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium fistulosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium sativumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavonoid glycosides  
Direct ParentFlavonoid 8-C-glycosides  
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
    • 

  • Hydroxyflavonoid
    • 

  • 3'-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Phenolic glycoside
    • 

  • Hexose monosaccharide
    • 

  • Glycosyl compound
    • 

  • C-glycosyl compound
    • 

  • Chromone
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Catechol
    • 

  • Phenol
    • 

  • Pyranone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Monosaccharide
    • 

  • Oxane
    • 

  • Vinylogous acid
    • 

  • Heteroaromatic compound
    • 

  • Secondary alcohol
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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-1.9ALOGPS
logP-4ChemAxon
logS-0.53ALOGPS
pKa (Strongest Acidic)1.26ChemAxon
pKa (Strongest Basic)7.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.89 m³·mol⁻¹ChemAxon
Polarizability17.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0126934  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016455  
KNApSAcK IDNot Available
Chemspider ID2788007  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3549960  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available