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Showing NP-Card for 7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one (NP0245783)

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Record Information
Version2.0
Created at2022-09-07 06:59:29 UTC
Updated at2022-09-07 06:59:29 UTC
NP-MRD IDNP0245783
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one
DescriptionExcavatin L 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). 7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one is found in Clausena excavata. Based on a literature review very few articles have been published on Excavatin L.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0245783 (7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one)


  Mrv1652309072208592D          

 26 29  0  0  1  0            999 V2000
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   -0.5521   -7.6921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649   -6.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 12 13  1  0  0  0  0
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 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
 16 26  1  0  0  0  0
M  END
Download

3D MOL for NP0245783 (7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one)

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3D SDF for NP0245783 (7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one)

  Mrv1652309072208592D          

 26 29  0  0  1  0            999 V2000
   -1.7590   -4.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4950   -4.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -4.9447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0652   -5.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4525   -6.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908   -7.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5521   -7.6921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2649   -6.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -6.6965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797   -5.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
    0.0000   -1.6500    0.0000 O   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
    0.7145   -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
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    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 25 26  2  0  0  0  0
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M  END
> <DATABASE_ID>
NP0245783

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C[C@H]2OC(=O)C(CO)=C2)OC1COC1=CC=C2C=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O7/c1-19(8-14-6-12(9-20)18(22)24-14)16(26-19)10-23-13-4-2-11-3-5-17(21)25-15(11)7-13/h2-7,14,16,20H,8-10H2,1H3/t14-,16?,19?/m0/s1

> <INCHI_KEY>
SREZIYPRWBLGDH-ASFAAARLSA-N

> <FORMULA>
C19H18O7

> <MOLECULAR_WEIGHT>
358.346

> <EXACT_MASS>
358.10525292

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.78378043099322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(3-{[(2R)-4-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]-2H-chromen-2-one

> <JCHEM_LOGP>
1.4068954933333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.970055688896988

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.288259012417736

> <JCHEM_PKA_STRONGEST_BASIC>
-2.854316862055386

> <JCHEM_POLAR_SURFACE_AREA>
94.59000000000002

> <JCHEM_REFRACTIVITY>
91.0107

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7-[(3-{[(2R)-4-(hydroxymethyl)-5-oxo-2H-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0245783 (7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one)
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PDB for NP0245783 (7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.283  -7.714   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.104  -6.724   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.924  -7.714   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.191  -9.230   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.122 -10.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.845 -11.698   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.170 -13.082   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.031 -14.359   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.361 -11.430   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.469 -12.500   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.576  -9.905   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.874  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12   13                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    2   13                                                       
CONECT   13   12    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25   16                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

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3D PDB for NP0245783 (7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one)
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SMILES for NP0245783 (7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one)
CC1(C[C@H]2OC(=O)C(CO)=C2)OC1COC1=CC=C2C=CC(=O)OC2=C1
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INCHI for NP0245783 (7-[(3-{[(2r)-4-(hydroxymethyl)-5-oxo-2h-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one)
InChI=1S/C19H18O7/c1-19(8-14-6-12(9-20)18(22)24-14)16(26-19)10-23-13-4-2-11-3-5-17(21)25-15(11)7-13/h2-7,14,16,20H,8-10H2,1H3/t14-,16?,19?/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC19H18O7
Average Mass358.3460 Da
Monoisotopic Mass358.10525 Da
IUPAC Name7-[(3-{[(2R)-4-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]-2H-chromen-2-one
Traditional Name7-[(3-{[(2R)-4-(hydroxymethyl)-5-oxo-2H-furan-2-yl]methyl}-3-methyloxiran-2-yl)methoxy]chromen-2-one
CAS Registry NumberNot Available
SMILES
CC1(C[C@H]2OC(=O)C(CO)=C2)OC1COC1=CC=C2C=CC(=O)OC2=C1
InChI Identifier
InChI=1S/C19H18O7/c1-19(8-14-6-12(9-20)18(22)24-14)16(26-19)10-23-13-4-2-11-3-5-17(21)25-15(11)7-13/h2-7,14,16,20H,8-10H2,1H3/t14-,16?,19?/m0/s1
InChI KeySREZIYPRWBLGDH-ASFAAARLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Clausena excavataLOTUS 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
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Pyranone
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • 2-furanone
    • 

  • Heteroaromatic compound
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Dihydrofuran
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP1.41ChemAxon
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area94.59 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity91.01 m³·mol⁻¹ChemAxon
Polarizability35.78 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00039194  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15485578  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]