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Showing NP-Card for (R)-Apiumetin glucoside (NP0049294)

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Record Information
Version2.0
Created at2022-03-17 21:10:09 UTC
Updated at2022-03-17 21:10:09 UTC
NP-MRD IDNP0049294
Secondary Accession NumbersNone
Natural Product Identification
Common Name(R)-Apiumetin glucoside
Description(R)-Apiumetin glucoside belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety (R)-Apiumetin glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (R)-Apiumetin glucoside has been detected, but not quantified in, green vegetables and wild celeries. This could make (R)-apiumetin glucoside a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049294 ((R)-Apiumetin glucoside)


  Mrv0541 05061310482D          

 29 32  0  0  0  0            999 V2000
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2168    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  4  1  0  0  0  0
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 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  2  0  0  0  0
 19 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 21  7  1  0  0  0  0
 22 13  2  0  0  0  0
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 28 13  1  0  0  0  0
 28 17  1  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
M  END
Download

3D MOL for NP0049294 ((R)-Apiumetin glucoside)

Download
3D SDF for NP0049294 ((R)-Apiumetin glucoside)

  Mrv0541 05061310482D          

 29 32  0  0  0  0            999 V2000
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2168    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  4  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  2  0  0  0  0
 19 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 21  7  1  0  0  0  0
 22 13  2  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 11  1  0  0  0  0
 26 18  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
 28 13  1  0  0  0  0
 28 17  1  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CC2=C(O1)C(OC1OC(CO)C(O)C(O)C1O)=C1OC(=O)C=CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O9/c1-8(2)11-6-10-5-9-3-4-13(22)28-17(9)19(18(10)26-11)29-20-16(25)15(24)14(23)12(7-21)27-20/h3-5,11-12,14-16,20-21,23-25H,1,6-7H2,2H3

> <INCHI_KEY>
VPAPSBNFWBXZLU-UHFFFAOYSA-N

> <FORMULA>
C20H22O9

> <MOLECULAR_WEIGHT>
406.3833

> <EXACT_MASS>
406.126382302

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
40.23015136480146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(prop-1-en-2-yl)-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
-0.00

> <JCHEM_LOGP>
0.1283216059999998

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.195995297663739

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199886092905503

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923662274655

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
98.56159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(prop-1-en-2-yl)-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H-furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049294 ((R)-Apiumetin glucoside)
Download
PDB for NP0049294 ((R)-Apiumetin glucoside)
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      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.804   5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.471   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.471   8.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.137   9.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.197   8.233   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.138   6.693   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.804   9.003   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.137  10.543   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.530   9.003   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.137   5.923   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    4    9                                                       
CONECT    4    3   13                                                       
CONECT    5    9   10                                                       
CONECT    6   10   11                                                       
CONECT    7   12   21                                                       
CONECT    8    1    2   11                                                  
CONECT    9    3    5   17                                                  
CONECT   10    5    6   18                                                  
CONECT   11    6    8   26                                                  
CONECT   12    7   14   27                                                  
CONECT   13    4   22   28                                                  
CONECT   14   12   15   23                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   20   25                                                  
CONECT   17    9   19   28                                                  
CONECT   18   10   19   26                                                  
CONECT   19   17   18   29                                                  
CONECT   20   16   27   29                                                  
CONECT   21    7                                                            
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   11   18                                                       
CONECT   27   12   20                                                       
CONECT   28   13   17                                                       
CONECT   29   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

Download
3D PDB for NP0049294 ((R)-Apiumetin glucoside)
Download
SMILES for NP0049294 ((R)-Apiumetin glucoside)
CC(=C)C1CC2=C(O1)C(OC1OC(CO)C(O)C(O)C1O)=C1OC(=O)C=CC1=C2
Download
INCHI for NP0049294 ((R)-Apiumetin glucoside)
InChI=1S/C20H22O9/c1-8(2)11-6-10-5-9-3-4-13(22)28-17(9)19(18(10)26-11)29-20-16(25)15(24)14(23)12(7-21)27-20/h3-5,11-12,14-16,20-21,23-25H,1,6-7H2,2H3
Download
View in JSmol
Synonyms
ValueSource
(-)-2,3-Dihydro-9-O-beta-glucosyloxy-2-isopropenyl-7H-furo[3,2-g][1]benzopyran-7-oneHMDB
Chemical FormulaC20H22O9
Average Mass406.3833 Da
Monoisotopic Mass406.12638 Da
IUPAC Name2-(prop-1-en-2-yl)-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,7H-furo[3,2-g]chromen-7-one
Traditional Name2-(prop-1-en-2-yl)-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H-furo[3,2-g]chromen-7-one
CAS Registry Number115356-05-3
SMILES
CC(=C)C1CC2=C(O1)C(OC1OC(CO)C(O)C(O)C1O)=C1OC(=O)C=CC1=C2
InChI Identifier
InChI=1S/C20H22O9/c1-8(2)11-6-10-5-9-3-4-13(22)28-17(9)19(18(10)26-11)29-20-16(25)15(24)14(23)12(7-21)27-20/h3-5,11-12,14-16,20-21,23-25H,1,6-7H2,2H3
InChI KeyVPAPSBNFWBXZLU-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apium graveolensFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassCoumarin glycosides  
Direct ParentCoumarin glycosides  
Alternative Parents
Substituents
  • Coumarin o-glycoside
    • 

  • Coumarin-8-o-glycoside
    • 

  • Phenolic glycoside
    • 

  • Furanocoumarin
    • 

  • Linear furanocoumarin
    • 

  • Psoralen
    • 

  • Hexose monosaccharide
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Coumaran
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Monosaccharide
    • 

  • Pyran
    • 

  • Oxane
    • 

  • Heteroaromatic compound
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Acetal
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Polyol
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Primary 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
logP0ALOGPS
logP0.13ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.56 m³·mol⁻¹ChemAxon
Polarizability40.23 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039039  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018536  
KNApSAcK IDC00019835  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14033997  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available