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Showing NP-Card for 8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate (NP0223014)

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Record Information
Version2.0
Created at2022-09-06 00:59:34 UTC
Updated at2022-09-06 00:59:34 UTC
NP-MRD IDNP0223014
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate
DescriptionEdulisin III belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Edulisin III is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Edulisin III has been detected, but not quantified in, green vegetables. This could make edulisin III a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0223014 (8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate)


  Mrv0541 05061312272D          

 28 30  0  0  0  0            999 V2000
    1.7675    1.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964    0.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8343    0.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581    0.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0720    0.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820    1.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9360    4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770    4.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4880    3.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    4.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964    1.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2212   -0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1290    4.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2331    2.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151    3.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4261    2.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8741    3.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0935    1.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9109    1.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2651    0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3927   -1.1121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081    3.6030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9109    2.7244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6456    2.1769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0671    3.1614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6254    1.4869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4366   -0.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  2  1  0  0  0  0
 11  6  1  0  0  0  0
 12  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  2  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 11  1  0  0  0  0
 21  4  1  0  0  0  0
 21  5  1  0  0  0  0
 21 19  1  0  0  0  0
 22 12  2  0  0  0  0
 23 15  2  0  0  0  0
 24 20  2  0  0  0  0
 25 14  1  0  0  0  0
 25 19  1  0  0  0  0
 26 15  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 27 20  1  0  0  0  0
 28 12  1  0  0  0  0
 28 21  1  0  0  0  0
M  END
Download

3D MOL for NP0223014 (8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate)

Download
3D SDF for NP0223014 (8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate)

  Mrv0541 05061312272D          

 28 30  0  0  0  0            999 V2000
    1.7675    1.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964    0.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8343    0.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4581    0.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0720    0.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820    1.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9360    4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770    4.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4880    3.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7700    4.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964    1.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2212   -0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1290    4.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2331    2.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151    3.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4261    2.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8741    3.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0935    1.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9109    1.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2651    0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3927   -1.1121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7081    3.6030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9109    2.7244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6456    2.1769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0671    3.1614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6254    1.4869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4366   -0.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  9  7  2  0  0  0  0
 10  8  2  0  0  0  0
 11  2  1  0  0  0  0
 11  6  1  0  0  0  0
 12  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  2  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 11  1  0  0  0  0
 21  4  1  0  0  0  0
 21  5  1  0  0  0  0
 21 19  1  0  0  0  0
 22 12  2  0  0  0  0
 23 15  2  0  0  0  0
 24 20  2  0  0  0  0
 25 14  1  0  0  0  0
 25 19  1  0  0  0  0
 26 15  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 27 20  1  0  0  0  0
 28 12  1  0  0  0  0
 28 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223014

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1C(OC2=C1C1=C(C=C2)C=CC(=O)O1)C(C)(C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O7/c1-6-11(2)20(24)27-18-16-14(25-19(18)21(4,5)28-12(3)22)9-7-13-8-10-15(23)26-17(13)16/h7-11,18-19H,6H2,1-5H3

> <INCHI_KEY>
UBLBUWKMSDCDLT-UHFFFAOYSA-N

> <FORMULA>
C21H24O7

> <MOLECULAR_WEIGHT>
388.4111

> <EXACT_MASS>
388.152203122

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.15090380367231

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[2-(acetyloxy)propan-2-yl]-2-oxo-2H,8H,9H-furo[2,3-h]chromen-9-yl 2-methylbutanoate

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
3.383739070999999

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9047493729965845

> <JCHEM_POLAR_SURFACE_AREA>
88.13000000000001

> <JCHEM_REFRACTIVITY>
99.65379999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[2-(acetyloxy)propan-2-yl]-2-oxo-8H,9H-furo[2,3-h]chromen-9-yl 2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0223014 (8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate)
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PDB for NP0223014 (8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate)
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       3.299   2.776   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.967   1.236   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.624   0.461   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.188   1.093   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.201   1.733   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.633   3.546   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.081   8.006   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.544   8.830   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.111   6.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.037   8.510   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.967   2.776   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.480  -0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.574   7.686   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.635   5.397   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.562   7.046   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.129   5.077   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.098   6.221   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.968   3.546   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.375   2.919   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.300   3.546   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.695   1.413   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.800  -2.076   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.055   6.726   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.300   5.086   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      12.405   4.064   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.592   5.901   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.634   2.776   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.015  -0.094   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   21                                                            
CONECT    5   21                                                            
CONECT    6    1   11                                                       
CONECT    7    9   13                                                       
CONECT    8   10   13                                                       
CONECT    9    7   14                                                       
CONECT   10    8   15                                                       
CONECT   11    2    6   20                                                  
CONECT   12    3   22   28                                                  
CONECT   13    7    8   17                                                  
CONECT   14    9   16   25                                                  
CONECT   15   10   23   26                                                  
CONECT   16   14   17   18                                                  
CONECT   17   13   16   26                                                  
CONECT   18   16   19   27                                                  
CONECT   19   18   21   25                                                  
CONECT   20   11   24   27                                                  
CONECT   21    4    5   19   28                                             
CONECT   22   12                                                            
CONECT   23   15                                                            
CONECT   24   20                                                            
CONECT   25   14   19                                                       
CONECT   26   15   17                                                       
CONECT   27   18   20                                                       
CONECT   28   12   21                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

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3D PDB for NP0223014 (8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate)
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SMILES for NP0223014 (8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate)
CCC(C)C(=O)OC1C(OC2=C1C1=C(C=C2)C=CC(=O)O1)C(C)(C)OC(C)=O
Download
INCHI for NP0223014 (8-[2-(acetyloxy)propan-2-yl]-2-oxo-8h,9h-furo[2,3-h]chromen-9-yl 2-methylbutanoate)
InChI=1S/C21H24O7/c1-6-11(2)20(24)27-18-16-14(25-19(18)21(4,5)28-12(3)22)9-7-13-8-10-15(23)26-17(13)16/h7-11,18-19H,6H2,1-5H3
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View in JSmol
Synonyms
ValueSource
3'-(2-Methylbutyryloxy)-4'-acetoxy-2',3'-dihydrooroselolHMDB
8-[2-(Acetyloxy)propan-2-yl]-2-oxo-2H,8H,9H-furo[2,3-H]chromen-9-yl 2-methylbutanoic acidGenerator
Edulisin IIIMeSH
Chemical FormulaC21H24O7
Average Mass388.4111 Da
Monoisotopic Mass388.15220 Da
IUPAC Name8-[2-(acetyloxy)propan-2-yl]-2-oxo-2H,8H,9H-furo[2,3-h]chromen-9-yl 2-methylbutanoate
Traditional Name8-[2-(acetyloxy)propan-2-yl]-2-oxo-8H,9H-furo[2,3-h]chromen-9-yl 2-methylbutanoate
CAS Registry NumberNot Available
SMILES
CCC(C)C(=O)OC1C(OC2=C1C1=C(C=C2)C=CC(=O)O1)C(C)(C)OC(C)=O
InChI Identifier
InChI=1S/C21H24O7/c1-6-11(2)20(24)27-18-16-14(25-19(18)21(4,5)28-12(3)22)9-7-13-8-10-15(23)26-17(13)16/h7-11,18-19H,6H2,1-5H3
InChI KeyUBLBUWKMSDCDLT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassFuranocoumarins  
Direct ParentAngular furanocoumarins  
Alternative Parents
Substituents
  • Angular furanocoumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Coumaran
    • 

  • Alkyl aryl ether
    • 

  • Fatty acid ester
    • 

  • Pyranone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Fatty acyl
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Heteroaromatic compound
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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
logP3.61ALOGPS
logP3.38ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area88.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.65 m³·mol⁻¹ChemAxon
Polarizability40.15 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0041197  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021096  
KNApSAcK IDC00019854  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91736606  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]