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Showing NP-Card for 9-Hydroxy-4-methoxypsoralen 9-glucoside (NP0049297)

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Record Information
Version2.0
Created at2022-03-17 21:10:14 UTC
Updated at2022-03-17 21:10:14 UTC
NP-MRD IDNP0049297
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-Hydroxy-4-methoxypsoralen 9-glucoside
Description9-Hydroxy-4-methoxypsoralen 9-glucoside, also known as 5-methoxy-8-O-beta-D-glucosyloxy-psoralen, 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. 9-Hydroxy-4-methoxypsoralen 9-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 9-Hydroxy-4-methoxypsoralen 9-glucoside has been detected, but not quantified in, green vegetables and wild celeries. This could make 9-hydroxy-4-methoxypsoralen 9-glucoside a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049297 (9-Hydroxy-4-methoxypsoralen 9-glucoside)


  Mrv0541 05061310482D          

 28 31  0  0  0  0            999 V2000
    0.0000   -1.6500    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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    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
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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
    2.2136    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  8  2  0  0  0  0
 16  7  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 19  6  1  0  0  0  0
 20 10  2  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 23 13  1  0  0  0  0
 24  1  1  0  0  0  0
 24 14  1  0  0  0  0
 25  5  1  0  0  0  0
 25 15  1  0  0  0  0
 26  9  1  0  0  0  0
 26 18  1  0  0  0  0
 27 10  1  0  0  0  0
 27 16  1  0  0  0  0
 28 17  1  0  0  0  0
 28 18  1  0  0  0  0
M  END
Download

3D MOL for NP0049297 (9-Hydroxy-4-methoxypsoralen 9-glucoside)

Download
3D SDF for NP0049297 (9-Hydroxy-4-methoxypsoralen 9-glucoside)

  Mrv0541 05061310482D          

 28 31  0  0  0  0            999 V2000
    0.0000   -1.6500    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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    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
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   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
    2.2136    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  8  2  0  0  0  0
 16  7  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 19  6  1  0  0  0  0
 20 10  2  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 23 13  1  0  0  0  0
 24  1  1  0  0  0  0
 24 14  1  0  0  0  0
 25  5  1  0  0  0  0
 25 15  1  0  0  0  0
 26  9  1  0  0  0  0
 26 18  1  0  0  0  0
 27 10  1  0  0  0  0
 27 16  1  0  0  0  0
 28 17  1  0  0  0  0
 28 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049297

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=CC(=O)OC2=C(OC2OC(CO)C(O)C(O)C2O)C2=C1C=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O10/c1-24-14-7-2-3-10(20)27-16(7)17(15-8(14)4-5-25-15)28-18-13(23)12(22)11(21)9(6-19)26-18/h2-5,9,11-13,18-19,21-23H,6H2,1H3

> <INCHI_KEY>
BPZBSASYSWKXFS-UHFFFAOYSA-N

> <FORMULA>
C18H18O10

> <MOLECULAR_WEIGHT>
394.3295

> <EXACT_MASS>
394.089996796

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
36.958234883211965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
-0.7868216646666673

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.195995075939187

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199885503142008

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923662391406

> <JCHEM_POLAR_SURFACE_AREA>
148.04999999999998

> <JCHEM_REFRACTIVITY>
90.97819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.96e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049297 (9-Hydroxy-4-methoxypsoralen 9-glucoside)
Download
PDB for NP0049297 (9-Hydroxy-4-methoxypsoralen 9-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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.132   2.016   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2    3    7                                                       
CONECT    3    2   10                                                       
CONECT    4    5    8                                                       
CONECT    5    4   25                                                       
CONECT    6    9   19                                                       
CONECT    7    2   14   16                                                  
CONECT    8    4   14   15                                                  
CONECT    9    6   11   26                                                  
CONECT   10    3   20   27                                                  
CONECT   11    9   12   21                                                  
CONECT   12   11   13   22                                                  
CONECT   13   12   18   23                                                  
CONECT   14    7    8   24                                                  
CONECT   15    8   17   25                                                  
CONECT   16    7   17   27                                                  
CONECT   17   15   16   28                                                  
CONECT   18   13   26   28                                                  
CONECT   19    6                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
CONECT   23   13                                                            
CONECT   24    1   14                                                       
CONECT   25    5   15                                                       
CONECT   26    9   18                                                       
CONECT   27   10   16                                                       
CONECT   28   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

Download
3D PDB for NP0049297 (9-Hydroxy-4-methoxypsoralen 9-glucoside)
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SMILES for NP0049297 (9-Hydroxy-4-methoxypsoralen 9-glucoside)
COC1=C2C=CC(=O)OC2=C(OC2OC(CO)C(O)C(O)C2O)C2=C1C=CO2
Download
INCHI for NP0049297 (9-Hydroxy-4-methoxypsoralen 9-glucoside)
InChI=1S/C18H18O10/c1-24-14-7-2-3-10(20)27-16(7)17(15-8(14)4-5-25-15)28-18-13(23)12(22)11(21)9(6-19)26-18/h2-5,9,11-13,18-19,21-23H,6H2,1H3
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View in JSmol
Synonyms
ValueSource
5-Methoxy-8-O-beta-D-glucosyloxy-psoralenHMDB
Chemical FormulaC18H18O10
Average Mass394.3295 Da
Monoisotopic Mass394.09000 Da
IUPAC Name4-methoxy-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7H-furo[3,2-g]chromen-7-one
Traditional Name4-methoxy-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}furo[3,2-g]chromen-7-one
CAS Registry Number115356-06-4
SMILES
COC1=C2C=CC(=O)OC2=C(OC2OC(CO)C(O)C(O)C2O)C2=C1C=CO2
InChI Identifier
InChI=1S/C18H18O10/c1-24-14-7-2-3-10(20)27-16(7)17(15-8(14)4-5-25-15)28-18-13(23)12(22)11(21)9(6-19)26-18/h2-5,9,11-13,18-19,21-23H,6H2,1H3
InChI KeyBPZBSASYSWKXFS-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
    • 

  • 5-methoxypsoralen
    • 

  • Phenolic glycoside
    • 

  • Furanocoumarin
    • 

  • Linear furanocoumarin
    • 

  • Psoralen
    • 

  • Hexose monosaccharide
    • 

  • Glycosyl compound
    • 

  • O-glycosyl compound
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Benzofuran
    • 

  • Anisole
    • 

  • Pyranone
    • 

  • Alkyl aryl ether
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Oxane
    • 

  • Monosaccharide
    • 

  • Heteroaromatic compound
    • 

  • Furan
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Ether
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Primary alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • 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
logP0.04ALOGPS
logP-0.79ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area148.05 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.98 m³·mol⁻¹ChemAxon
Polarizability36.96 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039047  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018544  
KNApSAcK IDC00019957  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14034001  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available