Np mrd loader

Showing NP-Card for 8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one (NP0330740)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-12 16:23:05 UTC
Updated at2022-09-12 16:23:05 UTC
NP-MRD IDNP0330740
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one
DescriptionMarshrin belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Marshrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Marshrin has been detected, but not quantified in, citrus. 8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one is found in Citrus aurantium. This could make marshrin a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0330740 (8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one)


  Mrv0541 05061307212D          

 21 24  0  0  0  0            999 V2000
    2.5382    1.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0174    2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4232    5.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0642    5.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752    4.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572    5.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6162    5.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203    3.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    4.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    3.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613    4.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584    2.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    2.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584    1.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    1.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    4.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    0.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2723    3.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    4.1803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433    2.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1593    2.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 15  1  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  2  0  0  0  0
 17 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
Download

3D MOL for NP0330740 (8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one)

Download
3D SDF for NP0330740 (8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one)

  Mrv0541 05061307212D          

 21 24  0  0  0  0            999 V2000
    2.5382    1.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0174    2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4232    5.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0642    5.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752    4.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572    5.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6162    5.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7203    3.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0023    4.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    3.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613    4.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584    2.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    2.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6584    1.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738    1.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953    4.6218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9133    0.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2723    3.2971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5543    4.1803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1433    2.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1593    2.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 15  1  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  2  0  0  0  0
 17 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C2OC(O)C3(C)OC23)C2=C(C=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O6/c1-15-13(21-15)12(20-14(15)17)10-8(18-2)5-3-7-4-6-9(16)19-11(7)10/h3-6,12-14,17H,1-2H3

> <INCHI_KEY>
VUIRVFUCVWAGFV-UHFFFAOYSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.2681

> <EXACT_MASS>
290.07903818

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.88626989245251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.2070936276666668

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.161791599547911

> <JCHEM_PKA_STRONGEST_BASIC>
-3.978864589409231

> <JCHEM_POLAR_SURFACE_AREA>
77.52000000000001

> <JCHEM_REFRACTIVITY>
71.36310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0330740 (8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one)
Download
PDB for NP0330740 (8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one)
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       4.738   2.092   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.366   4.690   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.257   9.908   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.720  10.732   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.287   8.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.213  10.412   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.750   9.588   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.811   7.299   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.738   8.948   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.305   6.979   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.274   8.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.829   5.514   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.364   5.038   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.829   3.023   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.364   3.498   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.231   8.627   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.305   1.558   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.842   6.155   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.768   7.803   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.734   4.268   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.031   4.268   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   18                                                            
CONECT    3    5    7                                                       
CONECT    4    6    7                                                       
CONECT    5    3    8                                                       
CONECT    6    4    9                                                       
CONECT    7    3    4   11                                                  
CONECT    8    5   10   18                                                  
CONECT    9    6   16   19                                                  
CONECT   10    8   11   12                                                  
CONECT   11    7   10   19                                                  
CONECT   12   10   13   20                                                  
CONECT   13   12   15   21                                                  
CONECT   14   15   17   20                                                  
CONECT   15    1   13   14   21                                             
CONECT   16    9                                                            
CONECT   17   14                                                            
CONECT   18    2    8                                                       
CONECT   19    9   11                                                       
CONECT   20   12   14                                                       
CONECT   21   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

Download
3D PDB for NP0330740 (8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one)
Download
SMILES for NP0330740 (8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one)
COC1=C(C2OC(O)C3(C)OC23)C2=C(C=CC(=O)O2)C=C1
Download
INCHI for NP0330740 (8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one)
InChI=1S/C15H14O6/c1-15-13(21-15)12(20-14(15)17)10-8(18-2)5-3-7-4-6-9(16)19-11(7)10/h3-6,12-14,17H,1-2H3
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC15H14O6
Average Mass290.2681 Da
Monoisotopic Mass290.07904 Da
IUPAC Name8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxy-2H-chromen-2-one
Traditional Name8-{4-hydroxy-5-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}-7-methoxychromen-2-one
CAS Registry NumberNot Available
SMILES
COC1=C(C2OC(O)C3(C)OC23)C2=C(C=CC(=O)O2)C=C1
InChI Identifier
InChI=1S/C15H14O6/c1-15-13(21-15)12(20-14(15)17)10-8(18-2)5-3-7-4-6-9(16)19-11(7)10/h3-6,12-14,17H,1-2H3
InChI KeyVUIRVFUCVWAGFV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Citrus aurantiumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassNot Available
Direct ParentCoumarins and derivatives  
Alternative Parents
Substituents
  • Coumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • Para-dioxane
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Monosaccharide
    • 

  • Heteroaromatic compound
    • 

  • Tetrahydrofuran
    • 

  • Hemiacetal
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Dialkyl ether
    • 

  • Oxirane
    • 

  • Ether
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • 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
logP1.63ALOGPS
logP1.21ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.16ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.36 m³·mol⁻¹ChemAxon
Polarizability27.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033783  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011941  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73193397  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]